Friday Weekly Q&A Call - 08/21/2026 · 🏠 Lower Taxes w/ Ryan

Lyn Cueto

26d • 📸 Recorded Calls

Friday Weekly Q&A Call - 08/21/2026

Link: https://www.skool.com/taxes/classroom/ec6893ee?md=dabf682ae9ed46cc9463c93f0f836be5

Here's a summary of the key takeaways from this Friday Q&A session:

Refund delays & IRS process

Large refunds (e.g., $25K+) can trigger extended IRS review, sometimes lasting a year or more.
The IRS pays interest (~7%) on delayed refunds.
The Taxpayer Advocate Service (TAS) can help escalate stuck refunds — file Form 911, and it's faster to email ([email protected]) than fax. Local TAS offices (e.g., Springfield, NJ) may offer in-person help.
CPAs can pull IRS updates via a Power of Attorney (Form 2848) and the tax practitioner hotline, though the IRS can take up to 90 days per response cycle.

Estimated tax payment strategy

If short-term rental (STR) losses/bonus depreciation are expected to offset business or W-2 income, it can make sense to skip estimated tax payments rather than pay now and wait for a refund later — avoids giving the IRS an interest-free loan.
Requires accurate P&L (business + STR) for a Q4 tax projection to confirm the offset will materialize.

§469 grouping election & material participation

Multiple STRs can be grouped together (the "Dash-4"/§469 grouping election) to meet the 500-hour material participation test in aggregate, even if a property management company runs one specific property.
Standard STR tests still apply: average stay ≤7 days, no personal use, etc.

Cost segregation timing

Do a cost seg study in your highest-income/highest-tax-bracket year to maximize the value of the write-off (37% bracket >> 10% bracket).

Sale of former primary residence (§121 exclusion)

Must have lived in the home 2 of the last 5 years (730+ days, non-consecutive OK) before sale to exclude gain (up to $250K single/$500K married).
If gain is under the exclusion cap, renovation/improvement records become unnecessary.
Depreciation recapture still applies for any rental period, taxed regardless of the exclusion (roughly 20–25% of depreciation taken).

W-2-heavy earners — limited offset options

Primary levers: max 401(k), IRA, HSA (only if enrolled in a high-deductible health plan — not to be confused with FSA's "use it or lose it" $300ish rollover cap).
Buying a short-term rental and tracking hours toward material participation is the biggest lever for offsetting W-2 income, but requires a purchase/loss to actually apply.
Marriage raises the standard deduction and itemization potential (mortgage interest capped at $750K in acquisition debt); only one primary residence can be claimed, though a second home's mortgage interest may still be deductible within limits.
Once income exceeds $150K, long-term rental losses generally can't offset W-2 income — STRs become the more effective strategy.
"Don't let the tax tail wag the dog" — don't buy real estate purely for tax reasons.

Real Estate Professional Status (REPS) with a full-time job

Requires 750+ hours AND more than 50% of total working time in real estate — difficult with a W-2 job, and hours spent on real estate while nominally on the clock for the W-2 job don't count (per tax court precedent).
A shifting work schedule (e.g., 4 months offshore/8 months home) can make REPS achievable if home-based hours clearly exceed W-2 hours.

Equipment-leasing bonus depreciation deals — caution

These were flagged on the IRS "Dirty Dozen" list; material participation is very hard to achieve with them despite aggressive marketing.
They can be legitimate as an offset to passive income only (no material participation needed), but claims of achieving material participation via trusts or leaseback structures are unproven/risky.
For mortgage qualification, a good lender will add back non-cash depreciation (including accelerated/cost-seg depreciation) when calculating income — but only if they know how to properly read a tax return.

1099 vs. payment method rules

2026 1099 threshold is $2,000 (up from $600).
Always collect a W-9 before paying a contractor to determine 1099 obligations.
No 1099 needed for payments to S-Corps/C-Corps, or for any payments made via credit card (card processor/merchant services handles reporting instead).
Regular LLCs (taxed as sole prop) and individuals still require a 1099 if the threshold is met and payment was via cash/check/Venmo/Zelle-type transfer.

Mixed-use property (office + STR) renovation

Leasing part of a property to your own management LLC as an office isn't tax-advantageous (commuting miles aren't deductible, and that portion is excluded from cost seg), but may still make sense if you'd be paying for outside office space anyway.
Cost segregation can still be applied proportionally to the STR-use portion of a mixed-use property (e.g., 75% Airbnb / 25% office → apply cost seg to the 75%).

General Mindset

Plan ahead, not reactively — match strategy to your actual bracket and cash flow, keep good documentation, and never let a tax break drive a major financial decision on its own. Be skeptical of any strategy that promises to wipe out your tax bill too easily.

Thank you all for joining!

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Friday Weekly Q&A Call - 08/21/2026