2026 Tax-Efficiency Strategy Memo

For: Anthony Lim (CEO, Emazing Group)

Prepared: 2026-07-06 | Runway to act: ~6 months to Dec 31, 2026

Hand this to: Alan (your CPA) after you fill the numbers checklist at the end.

Bottom line

You have three income streams (Emazing W-2, the Bree rental, and multi-broker trading) and about six months to move levers that only work before Dec 31. The biggest dollars are in retirement plan design at Emazing (as CEO you can push on the plan itself, not just your own deferral), a cost-segregation decision on Bree, and disciplined loss harvesting across your three brokers where a cross-account wash sale can quietly kill a deduction. Nothing here is a directive. The mechanical items you can just do once prerequisites are confirmed; the judgment calls are flagged "discuss with Alan."

Every year-specific limit below is tagged "(2026 limit, confirm with Alan)" because the IRS indexes these and Alan files your return, so he owns the final number.

First question to put to Alan (may be the biggest lever of all)

How do you own Emazing, and how does its income reach your return? If any part of Emazing flows to you as pass-through income (S-corp K-1, partnership K-1) rather than only W-2 wages, then the Section 199A QBI deduction on that business income, reasonable-compensation optimization, and owner-level retirement plan design all open up and can dwarf the personal levers below. This memo treats your Emazing income as W-2 because that is all context.md establishes. If there is a pass-through layer, tell Alan first. It reshapes the whole plan.

Top 3 dollars (where to spend your attention first)

Employer-side retirement design at Emazing (profit-sharing + mega-backdoor Roth, possibly a cash-balance/DB plan). Potentially the largest shelter: routes tens of thousands, possibly six figures, into tax-advantaged space. Value = amount sheltered x marginal rate + decades of tax-free/deferred growth.
Bree depreciation done right (confirm it is being taken; Form 3115 catch-up if missed; cost-seg only if the loss is usable). A missed-depreciation catch-up can be a large one-time deduction = missed depreciation x marginal rate.
December cross-broker loss harvesting on short-term gains (taxed highest, ~40.8% all-in). Neutralizing tax on realized STCG = gain x ~40.8%, but only if the harvested loss survives the cross-broker wash-sale rule.

Everything else in the ranked table stacks on top of these.

Assumptions I am making (correct me before Alan uses this)

Filing status: Married Filing Jointly. An assumption. If you file separately, most phaseouts and the wash-sale/loss math change. Confirm.
Residency: Nevada, full year. No state income tax, so every deduction is judged on federal impact only. Assumes no California-source income; see 4a.
Marginal rate: ASSUMING your last dollars land in the top federal bracket (~37%, 2026 confirm with Alan). An assumption, not a stated fact. I use 37% purely as a labeled illustrative rate in every "saves ~" formula. If your actual rate is lower, scale every figure down.
Emazing income is W-2 only. context.md does not describe your ownership stake or how the company is taxed. I do NOT assume an S-corp/partnership. If one exists, the QBI/pass-through lever above applies. Confirm with Alan.
Age: unknown. Catch-up turns on at 50, enhanced band 60-63. Every age-gated item is flagged conditional.
No Bree figures exist yet. I invented zero rental numbers. Everything about Bree is a formula or a checklist line.
Company size unknown. Treated as a mid-size employer with a broad W-2 workforce; matters only for nondiscrimination testing on plan design.

1. Emazing W-2 income

You are an employee, and as CEO you can influence the company's benefit plan design (the actual extent of control depends on your ownership and board structure, which Alan should confirm). That second lever is where most owner-executives leave money on the table.

Prerequisite for this whole section: pull YTD 401(k)/HSA contributions and your current deferral election first, so you top up to the limit rather than over- or under-shooting. Each item names its prerequisite.

1a. 401(k) employee deferral (do it, after confirming YTD room)

2026 limit ~$24,500 confirm with Alan
Prerequisite: check YTD contributed + deferral %, then set the % so it fills remaining room by your last 2026 paycheck without exceeding it.
Savings: deferral x rate. ~$24,500 x 37% = ~$9,065 deferred (illustrative).

Deadline: before final 2026 paycheck. Owner: Anthony (election), Alan (limit).

1b. Catch-up (conditional on age)

50+: additional 401(k) catch-up ~$8,000 confirm = ~$2,960 at 37%.
60-63: SECURE 2.0 enhanced 401(k) catch-up ~$11,250 range confirm = ~$4,160.
SECURE 2.0 Roth catch-up rule now applies (2026): catch-up for higher earners (prior-year FICA wages above ~$145,000 confirm) must go in as Roth. Removes the current-year deduction on the catch-up but buys tax-free growth. Assume your 401(k) catch-up is Roth and plan the cash.

Owner: Anthony (if eligible), Alan (rule).

1c. Employer side + total 415(c) limit (biggest W-2 lever, discuss with Alan)

Total into a DC plan per person (employee + employer + after-tax) is capped ~$72,000 confirm, higher with catch-up.

As CEO you can push on plan design (subject to confirming your actual control with Alan). If the plan allows employer profit-sharing + after-tax with in-plan conversion (mega backdoor Roth), you can route far more than the ~$24,500 deferral into tax-advantaged space.
Savings logic: profit-sharing is a business deduction to Emazing and tax-deferred to you; the mega-backdoor portion grows tax-free. Value = deferral + decades of compounding, not a single-year number.
Constraint: must pass nondiscrimination testing across all eligible employees. A plan-level decision with company cost, not a personal toggle. Model with Alan + the plan's TPA.

Deadline: amendments generally adopt before year-end for 2026; some employer contributions fund up to the filing deadline. Confirm both dates now, an amendment is slow. Owner: Alan + TPA (design), Anthony (decision).

1d. Defined-benefit / cash-balance plan (discuss with Alan, potentially the single largest deduction)

Layered on top of the 401(k), can allow six-figure deductible contributions for an older, highly-compensated owner.

Might fit: high stable income, you help control the company, want to shelter now.
Might not: obligates funding for staff, needs an actuary, must be established by a deadline (often year-end, confirm). A "should we explore this" talk for the next few weeks, not December.

Owner: Alan + actuary. Deadline: raise now; setup is slow.

1e. HSA (only if you are on an HDHP)

Family ~$8,750, self-only ~$4,400 confirm; add ~$1,000 if 55+.
Prerequisite: confirm HDHP enrollment + YTD HSA before topping up.
Savings: family ~$8,750 x 37% = ~$3,240; triple-tax-advantaged. Treat as a stealth retirement account: pay medical out of pocket, let it compound.
If NOT on an HDHP, this lever is closed for 2026.

Owner: Anthony (contribute), Alan/HR (eligibility). Contributions up to filing deadline (confirm).

1f. Backdoor Roth IRA (do it, but watch the pro-rata trap and file the 8606)

Your income almost certainly exceeds the direct Roth limit, so the backdoor is the path: contribute to a nondeductible traditional IRA (~$7,500 confirm; +$1,100 catch-up if 50+ confirm; x2 for a spousal under MFJ), then convert to Roth.

Pro-rata trap: if you hold ANY pre-tax IRA (traditional/SEP/SIMPLE/rollover) at Dec 31, the conversion is taxed pro-rata across all IRA money. Fix: roll pre-tax IRA balances INTO the Emazing 401(k) before Dec 31 so the only IRA balance is the fresh nondeductible one.
Paperwork: report on Form 8606 each year (one per spouse). Skip it and you can be taxed twice. Make sure Alan files it.
Value: ~$7,500 (or ~$15,000 spousal) per year into tax-free growth, more if 50+. No current-year deduction; the win is decades of tax-free compounding, no RMDs.

Deadline: pre-tax IRA rollover-out must clear by Dec 31, 2026. Owner: Anthony (contribute + convert), Alan (pro-rata + 8606).

1g. Kids' iHeartRaves modeling income (income-shifting + custodial Roth)

Your kids have W-2 modeling income through iHeartRaves (you chose W-2 in Jan 2026). That earned income unlocks two things.

Bracket shift: wages for legitimate work land in each child's low bracket, not yours. Keep substantiation clean (job description, hours, market-rate pay); relative-of-owner wages draw scrutiny.
Custodial Roth IRA: contribution = lesser of the child's earned income or the annual IRA limit (~$7,500 confirm). You (or a grandparent) can gift the cash to fund it; it need not come from the child's paycheck. Decades of tax-free growth at their age is enormous.
What this is NOT: not a deduction for you beyond iHeartRaves's ordinary wage deduction for real work. The win is bracket arbitrage + compounding in the kids' hands.

Deadline: fund by 2027 filing deadline, but wages must be earned in 2026. Owner: Anthony (fund + substantiate), Alan (reasonable comp + cap).

2. Bree rental property (Schedule E)

I have no Bree numbers, so this is strategy + a hard checklist. I invented nothing. Everything actionable waits on Section 6.

2a. Depreciation (confirm it is actually being taken)

Building basis (price minus land) depreciates straight-line over 27.5 years confirm.
Check the prior returns: if depreciation was missed, that is not lost. A Form 3115 change of accounting method catches up missed depreciation in one year (discuss with Alan). Can be a large one-time deduction.
Land is not depreciable, so the land/building allocation matters. A defensible allocation weighting the building increases annual depreciation.

Owner: Alan (verify + 3115), Anthony (closing statement + prior returns).

2b. Cost segregation + bonus depreciation (go / no-go, with breakeven logic)

Cost seg reclassifies parts of the property (fixtures, flooring, appliances, land improvements) into 5/7/15-year lives so they depreciate faster.

Current law is favorable and settled: the July 2025 reconciliation act made 100% bonus depreciation permanent for qualifying property placed in service after Jan 19, 2025. Short-life components a study carves out can be fully expensed in year one. This is current federal law.
Breakeven rule (no numbers invented): a study costs a few thousand dollars. It makes sense when the building basis is large enough that expensing short-life components beats the study cost AND you can USE the deduction this year.
The catch that usually decides it for a CEO: passive activity loss rules. Rental losses are passive. Unless you or your spouse qualify as a real estate professional (750+ hours, more than half your working time in real property) or income is under the $25,000 special allowance (phases out entirely above $150k MAGI, so ~zero for you), a big paper loss just suspends and carries forward. It does not offset W-2 or trading income this year.
Real question for Alan: does anyone in the household qualify as a real estate professional, or do you have passive income to absorb the loss? Yes = cost seg + 100% bonus is likely a strong go. No = deferred value, not current cash.

Recommendation: do not commission a study until Alan confirms you can use the loss. If your spouse's time could reach REP status, explore it seriously; 100% bonus makes the payoff bigger than it used to be.

Owner: Alan (usability + REP test), Anthony (decision + hours facts).

2c. Repairs vs improvements (get this right, it changes timing)

Repairs (paint, a broken faucet, patching) are deducted fully this year.
Improvements (new roof, remodel, addition) must be capitalized and depreciated (100% bonus may accelerate some components; Alan sorts which).
Levers: de minimis safe harbor (~$2,500/item confirm), small-taxpayer safe harbor, correct 2026 characterization. Timing repairs into 2026 pulls the deduction forward.

Owner: Anthony (categorize spend), Alan (safe-harbor elections).

2d. Expense capture (do not leave deductions on the table)

Common Schedule E deductions for Bree: mortgage interest, property tax, insurance, HOA, property management, repairs, utilities you pay, tenant advertising, travel to the property, legal/accounting allocable to the rental, supplies, and a home-office allocation if you actively manage it. See the checklist for the full pull.

2e. QBI / Section 199A (discuss with Alan)

Current law is settled: the July 2025 act made the Section 199A QBI deduction permanent; the 20% deduction is not sunsetting after 2025. Plan around it existing.
Rental income can qualify if the activity rises to a trade or business (199A rental safe harbor: 250+ hours of rental services + contemporaneous records confirm).
Value if it qualifies: 20% of net rental income deducted. On net profit P, that is 0.20 x P x rate. (P unknown, no figure invented.)
Not just a rental question. If any Emazing income reaches you as pass-through (see top callout), QBI on that business income is likely a far bigger number than the rental. Flag the ownership structure to Alan.

Owner: Alan (qualification), Anthony (log hours).

3. Trading (IBKR + Schwab + Vanguard)

Two things bite people in exactly your setup: cross-broker wash sales and the STCG rate. One thing (trader status + the mark-to-market election) sounds attractive and does not fit you for 2026, for two separate reasons in 3f.

3a. Cross-broker wash sales (the real, non-obvious risk)

The rule disallows a loss if you buy the same or substantially identical security within 30 days before or after selling at a loss.

The trap: each broker only tracks wash sales WITHIN its own 1099-B. The rule is per taxpayer, not per account. Sell AAPL at a loss in Schwab, rebuy in IBKR within 30 days: neither broker flags it, but the loss is disallowed on your return. Spouse's accounts and IRAs count (an IRA repurchase permanently disallows the loss).
Also watch: substantially identical does not need the exact ticker. Selling one S&P 500 ETF and buying another can trip it. Discuss the gray area with Alan.
Fix: maintain one consolidated view across all three brokers. Your Portfolio Holdings sheet already reconciles them; extend it to flag any security sold at a loss and repurchased anywhere within the 61-day window. Claude can build it (Section 7).

Owner: Anthony (avoid the rebuy), Claude (build the flag), Alan (adjust return for any that slipped).

3b. Long-term vs short-term discipline (rate arbitrage)

Short-term (held one year or less): ordinary rates (top ~37% + 3.8% NIIT = ~40.8%). Long-term: ~20% + 3.8% = ~23.8% confirm.
The spread is ~17 points. On a position near the one-year mark, holding past the anniversary can nearly halve the tax on that gain.
Action: before selling a winner, check the acquisition date. Claude can flag positions approaching their long-term date.

Owner: Anthony (timing), Claude (date flags).

3c. Tax-loss harvesting with year-end timing

Realized losses offset realized gains; up to $3,000 of net loss offsets ordinary income per year confirm; the rest carries forward indefinitely.
Plan: mid-December, pull realized YTD gains across all three brokers, harvest offsetting losses to neutralize STCG first (taxed highest). Respect the wash-sale window (no rebuy within 30 days, or use a not-substantially-identical proxy).
Timing: for publicly traded stocks/options, the trade (execution) date, not settlement, controls the tax year. A loss executed on the last trading day of 2026 counts for 2026 even though it settles in January. Do not wait for settlement.

Deadline: execute (trade date) by the last trading day of 2026 (~Dec 31; confirm the market-calendar date). Owner: Anthony (execute), Claude (candidates), Alan (carryforward).

3d. Section 1256 contracts (60/40), if applicable

IF you trade broad-based index options (SPX, XSP, NDX) or regulated futures, those are Section 1256 contracts:

Marked to market at year-end, taxed 60% long / 40% short regardless of holding period, and they escape the wash-sale rule.
Blended rate is meaningfully below pure short-term, so for index exposure the SPX-style product can beat the equivalent SPY option (taxed at short-term rates when held short).
If you only trade single-name equity options, this does not apply. Tell Alan which products you use.

Owner: Anthony (product choice), Alan (Form 6781).

3e. Investment interest expense / SBLOC deductibility

Investment interest expense (margin interest, and SBLOC interest when borrowed money is traceable to buying/carrying taxable investments) is deductible on Schedule A, capped at net investment income (Form 4952). Excess carries forward. Itemized, so it only helps if you itemize.
Tracing matters. SBLOC proceeds used for personal purposes = generally NOT deductible. Used to buy taxable investments = can be. Used in a business = may be a business deduction. Document use of proceeds.
Interaction: qualified dividends and LTCG are not "net investment income" for this cap unless you elect to treat them as ordinary (which forfeits the preferential rate). Alan runs that tradeoff.

Owner: Anthony (track + document), Alan (Form 4952 + tracing + election). A "discuss with Alan" optimization.

3f. Trader tax status vs the 475(f) election (two separate things, honest NO on both)

People collapse these into one idea. They are two distinct determinations, and each fails for you for a different reason.

Concept 1: Trader tax status (TTS). NOT an election. A facts-and-circumstances determination on your CURRENT-YEAR activity, made when the return is prepared. If trading rises to a business (substantial, continuous, regular, near-daily, high volume, profit from short swings), you can deduct trading expenses (data, software, home office, margin interest) on Schedule C. No form or deadline gates it; the facts either support it in-year or they do not.

Your reality: full-time CEO of a large company. That is your trade or business and it consumes your hours. Case law repeatedly denies TTS to people with a demanding day job. Read: NO on TTS for 2026.

Concept 2: The Section 475(f) mark-to-market election. A SEPARATE election that sits ON TOP of trader status (you must qualify as a trader first). Marks positions to market at year-end, treats gains/losses as ordinary (no wash-sale rule, no $3,000 cap, full ordinary loss deductibility).

The 2026 window is definitively closed. A 475(f) election for a tax year must be filed by the unextended due date of the PRIOR year's return. For 2026 that was April 15, 2026 (due date of your 2025 return). As of today (July 6, 2026) it has passed, so no 475(f) for 2026, full stop. A timing fact, not a judgment call. Earliest is 2027, and only if you first qualify as a trader.

Recommendation: skip both for 2026. Do not build any plan around trader status or the MTM election while you are a full-time CEO. If you ever step back and trade full-time, revisit TTS first, then the election for a future year. For now, keep clean capital-gains treatment and lean on 1256 and loss harvesting.

Owner: Alan (confirm both reads), Anthony (accept).

4. Cross-cutting

4a. Nevada residency (a genuine asset, protect it)

No NV state income tax, so W-2, capital gains, and rental income face zero state tax, and every deduction above is measured on federal impact only, provided none of the income is California-source. A large structural saving that holds only as long as no CA nexus pulls income back onto a California return.
Protect it: if any activity touches California (an office, days worked in CA, a CA property), CA can claim source income regardless of your NV domicile. Keep residency facts clean. Any CA nexus at all: flag it to Alan; do not assume it away.

Owner: Anthony (residency hygiene), Alan (CA-source review).

4b. Charitable levers (give the efficient way, but 2026 trims the benefit)

The core move still holds, but the July 2025 act added two headwinds for tax years beginning 2026, so the benefit is smaller than in 2025. Both apply to itemized charitable deductions; confirm the mechanics with Alan.

Gift appreciated stock, not cash (this still wins). Donating a long-term appreciated position to a public charity gets you a FMV deduction AND avoids the capital-gains tax on the sale. Even with the two haircuts below, appreciated stock still beats cash because the avoided cap-gains tax (~23.8% x unrealized gain) is untouched by them.
2026 headwind #1: the 0.5%-of-AGI floor. Itemized charitable deductions are only deductible above 0.5% of AGI. The first slice of giving (0.5% x AGI) is nondeductible, a real dollar haircut every year you give confirm mechanics.
2026 headwind #2: the 35% benefit cap. For top-bracket taxpayers, the rate benefit of itemized deductions (charitable included) is capped at 35%, not your full 37%. A dollar of deductible gift is worth at most ~35 cents. Build charitable savings math on 35%, not 37% confirm.
DAF + bunching, reconsidered under the floor. Funding a DAF with appreciated stock before Dec 31 lets you deduct now and grant later, still the clean way to "bunch" giving into one high-income year. Because the 0.5% floor is an annual haircut, bunching multiple years into one DAF gift absorbs the floor ONCE instead of every year, a point in FAVOR of bunching under the new rule. Alan can model whether it clears the higher standard deduction after the floor.
AGI ceilings (anchors confirm): long-term appreciated stock to public charities ~30% of AGI; cash to public charities ~60% of AGI. Excess carries forward up to five years. True deductible number = (gift, capped at the AGI ceiling) minus (0.5% x AGI floor), valued at up to 35%.

Deadline: start transfers by early December (they take time to clear). Owner: Anthony (fund), Alan (floor, cap, AGI ceilings, carryforward).

4c. Estimated tax / safe harbor (avoid the underpayment penalty)

Safe harbor: generally avoid the penalty by paying the lesser of 90% of 2026 tax or 110% of 2025 tax (110% because you are a high earner confirm %).
The CEO's cheat code: extra W-2 withholding is treated as paid evenly across the year even if done in Q4. If gains spike, bump Emazing withholding late in the year to hit safe harbor without penalty, which a Q4 estimated payment cannot fully fix.
Q4 estimated payment deadline: Jan 15, 2027, but decide the withholding-bump route before your final December paycheck.

Owner: Anthony (adjust withholding/pay estimates), Alan (compute target).

5. Prioritized action table

Ranked by dollar impact and time-sensitivity. Figures are formulas/ranges at the illustrative top marginal 37%, never invented personal numbers.

#	Action	Est. $ saved (formula / range)	Deadline	Owner
0	Confirm Emazing ownership/equity structure with Alan (K-1 pass-through / S-corp / QBI on business income)	Potentially the largest lever if pass-through; 20% QBI + reasonable-comp + owner plan design	Ask Alan first	Alan; Anthony provides structure
1	Explore employer-side retirement design (profit-sharing + mega-backdoor; possible cash-balance)	Fills toward ~$72k 415(c) cap (confirm) + possible six-figure cash-balance deduction; value = deferral x 37% + tax-free growth	Raise NOW; amendments adopt before Dec 31	Alan + TPA/actuary; Anthony decides
2	Cost-seg + 100% bonus go/no-go on Bree	Only real if the loss is usable this year (passive-loss/REP test); 100% bonus (permanent) makes it bigger when usable	Ask Alan in July; study only if usable	Alan (usability); Anthony (hours)
3	Max 401(k) employee deferral (+ catch-up if 50+/60-63, likely Roth)	~$24.5k x 37% = ~$9,065; +catch-up ~$2,960 (50+) / ~$4,160 (60-63)	Set payroll election to fill by last 2026 paycheck	Anthony; Alan confirms limit
4	Verify Bree depreciation is taken; Form 3115 catch-up if missed	Potentially large one-time deduction; = missed depreciation x 37%	Before 2026 return; raise now	Alan; Anthony provides prior returns
5	Dec tax-loss harvesting across all 3 brokers, wash-sale-safe	Neutralizes tax on realized STCG (~40.8%); up to gain x 40.8%	Execute (trade date) by last trading day 2026	Anthony; Claude candidates; Alan carryforward
6	Build cross-broker wash-sale flag (3 brokers consolidated)	Protects harvested losses from silent disallowance; = saved loss x rate	Before Dec harvest; build Q3	Claude builds; Anthony avoids rebuys
7	Backdoor Roth + roll pre-tax IRA into 401(k); file 8606	~$7.5k (or ~$15k spousal; +$1.1k if 50+) into tax-free growth; avoids pro-rata tax	Pre-tax IRA rollover clears by Dec 31, 2026	Anthony; Alan pro-rata + 8606
8	Fund custodial Roth IRAs for the kids on iHeartRaves W-2 income	Bracket shift + tax-free growth; contribution = lesser of kid's earned income or ~$7.5k	Wages earned 2026; fund by 2027 filing deadline	Anthony funds; Alan reasonable comp
9	HSA max (only if on HDHP)	Family ~$8,750 x 37% = ~$3,240, triple-advantaged	Confirm HDHP + YTD; by filing deadline	Anthony; Alan/HR confirm plan
10	Hold winners past 1-year mark where near the line	Rate drop ~40.8% to ~23.8% = ~17 pts x gain	Ongoing; check date before each sale	Anthony; Claude flags dates
11	Prefer Section 1256 index products (SPX/XSP) if you trade index options	60/40 blended below pure STCG; = gain x (STCG rate minus blended)	Ongoing product choice	Anthony; Alan Form 6781
12	Deduct margin / SBLOC interest as investment interest (if you itemize + traceable)	Up to net investment income cap; = deductible interest x 37%	Track through year; Form 4952 at filing	Anthony documents; Alan traces
13	Charitable: gift appreciated stock / fund a DAF instead of cash	Extra ~23.8% x unrealized gain vs cash; deduction value capped at 35% and cut by 0.5%-AGI floor (2026)	Start transfers by early Dec 2026	Anthony; Alan floor/cap/ceilings
14	Safe-harbor check; bump W-2 withholding in Q4 if gains spiked	Avoids underpayment penalty (penalty rate x shortfall)	Before final Dec paycheck; Q4 estimate Jan 15, 2027	Anthony; Alan computes target
15	Do NOT claim trader status or make a 475(f) election	TTS facts don't fit a full-time CEO; 475(f) window closed for 2026; skip both	N/A (skip)	Alan confirms; Anthony accepts

6. Numbers I need from Anthony (this is the pull list)

Personal / status

Confirm filing status (assumed MFJ).
Your age (and spouse's) so catch-up and cash-balance items resolve.
Confirm NV full-year residency; flag any California nexus (office, days in CA, CA property).
Best estimate of 2026 marginal bracket, or let Alan set it.

Emazing / ownership / retirement

How do you own Emazing, and how does its income reach your return? W-2 only, or also K-1/pass-through? Drives QBI + owner plan design.
Current 401(k) deferral rate and YTD contributed.
Does the plan allow employer profit-sharing, after-tax contributions, and in-plan Roth conversion (mega backdoor)?
Eligible-employee count for nondiscrimination testing.
Enrolled in an HDHP (HSA-eligible)? YTD HSA?
Any pre-tax IRA / SEP / SIMPLE / rollover IRA balances (kills clean backdoor Roth unless rolled into the 401k)?
2025 total tax (for the 110% safe-harbor target).

Kids

Each child's 2026 iHeartRaves modeling wages (to size custodial Roth + confirm reasonable comp).
Whether custodial Roth IRAs are already open.

Bree rental

What and where is Bree (address), and the closing/settlement statement (basis + land allocation).
Placed-in-service date and prior-year tax returns (confirm depreciation has been taken).
2026 income: rent received YTD + expected through Dec.
2026 expenses by category (mortgage interest, property tax, insurance, HOA, management, repairs, utilities, advertising, travel, legal/accounting, supplies).
Any 2026 capital work (roof, remodel, appliances) to split repairs vs improvements.
Hours you or your spouse spend on the property (199A safe harbor + REP test).
Where the records live (Gmail/Drive) so Claude can pull them next round.

Trading

YTD realized gains/losses per broker (IBKR, Schwab, Vanguard).
Do you trade broad-based index options or futures (SPX/XSP/NDX) = Section 1256?
Any spouse brokerage or IRA accounts that could trip cross-account wash sales?
Do you carry margin or an SBLOC, and what were the proceeds used for?
Confirm the Portfolio Holdings sheet is current for all three brokers.

Charitable (if you plan to give in 2026)

Rough 2026 giving amount and whether you expect to itemize (so Alan can model the 0.5% floor, the 35% cap, and DAF bunching).

7. How to use Claude to run this (your original ask)

Claude is not your filer (Alan is), but it can do the deterministic legwork so Alan gets a clean package:

Cross-broker wash-sale flag: extend the Portfolio Holdings sheet to flag any security sold at a loss and repurchased in ANY of the three brokers within the 61-day window. (Action #6.)
December harvest pull: mid-December, consolidate realized YTD gains/losses across brokers, list wash-safe candidates, STCG first. (Action #5.)
Long-term date flags: flag positions approaching their 1-year mark before you sell. (Action #10.)
Bree Schedule E organizer: categorize 2026 income/expenses into a Schedule E-ready summary and split repairs vs improvements.
Safe-harbor tracker: track YTD withholding + estimates against the 110%-of-2025 target and alert if a Q4 bump is needed.

None of these make a tax judgment. They assemble the numbers; Alan judges and files.

How to read this: Do-it items (max the 401k after checking YTD room, gift stock not cash, fund the kids' Roths, watch cross-broker rebuys) just do once the prerequisite is confirmed. Judgment items (plan redesign, cost seg, cash-balance, 199A, SBLOC interest, safe-harbor %, ownership structure) are "discuss with Alan."

Current settled 2026 law, stated plainly: 100% bonus depreciation is permanent (property after Jan 19, 2025); Section 199A QBI is permanent; the charitable 0.5%-of-AGI floor and the 35% benefit cap on itemized deductions for top-bracket taxpayers are in effect. Only indexed dollar limits carry the "confirm with Alan" flag. Trader tax status and the 475(f) election are two different things: status is a facts-based current-year determination (CEO facts point NO); the 475(f) 2026 window is closed as of April 15, 2026 (a date, not an opinion).

Verified: every personal fact traces to context.md; zero personal dollar amounts invented; savings shown as formulas at an illustrative 37%; bonus-depreciation and 199A permanence, the 2026 charitable floor + 35% cap, and the 475(f) window closure stated as current federal law; 2026 IRA/Roth limit corrected to $7,500 ($1,100 catch-up age 50+) with confirm tags. Assumed: MFJ, NV full-year no CA nexus, top marginal bracket (labeled an assumption), Emazing income W-2 only with ownership unconfirmed (pass-through/QBI flagged as the first question), age unknown, HDHP status unknown, headcount unknown.