Friday Weekly Q&A Call - 09/11/2026 · 🏠 Lower Taxes w/ Ryan

Friday Weekly Q&A Call - 09/11/2026

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

Cost Segregation & Timing

Cost seg studies don't have to happen the year of purchase — you can defer to a later year, but it requires Form 3115 (prepared by the cost seg company) to "catch up" the depreciation.
Best practice: time the cost seg study to your highest income year to maximize the tax benefit.
CSSI was recommended for larger/fully engineered studies; ReCostSeg for smaller properties or software-based studies. Six weeks with no completed study was flagged as too long a turnaround.

S-Corp Payroll & Safe Harbor Strategy

W-2 withholding is treated as paid evenly throughout the year regardless of when it's actually withheld — so a lump-sum "bonus paycheck" late in the year with heavy withholding can still avoid underpayment penalties (unlike estimated payments, which are date-sensitive).
Safe harbor target is generally 110% of prior year's tax liability (line 24).
Solo 401(k) employer contribution limits: 20% of net income for sole prop/single-member LLC/partnership vs. 25% of W-2 wages for S-corp/C-corp — described as a built-in "bonus" for incorporating.

Oil & Gas Investments (as a passive alternative to STR)

Intangible drilling costs can offset 75–90% of the investment depending on whether the well is already online (equipment/bonus depreciation available) vs. still raising funds (intangible costs only, ~75-85%).
Typical minimums ~$50K; requires unlimited personal liability (can't invest through an LLC) to qualify for the deduction.
Typical hold period 4–7 years; described as high-risk/high-return (mentioned ~20-40% IRR).
Can write a check as late as 12/31 and still claim the deduction for that tax year — used as a fallback "Plan B" when an STR purchase falls through.

Cost Segregation Mechanics — Decks, Furniture, Assets

Classification matters for bonus depreciation: structural elements (attached balconies, decks required for access) depreciate over the life of the building and don't qualify for bonus; land improvements (freestanding decks, gazebos, hot tub pads) do qualify.
Furniture/assets already depreciated can't be "re-depreciated" by moving them to a new property — but donating old furniture (vs. selling it) avoids a taxable recapture event while still generating a deduction.
Partial asset disposition: furnishing a property with old furniture first, then swapping in new furniture, allows depreciation on both rounds.

1031 Exchanges

Bonus depreciation doesn't reset in a 1031 — the "essence" of the old property's depreciation carries over.
You can split 1031 proceeds across multiple replacement properties, but you can only apply new cost segregation/bonus depreciation to the excess amount invested above what was rolled over (not the full purchase price).
Taking on additional debt to acquire more property than the exchange value creates boot (taxable).

Hiring Kids in an STR Business

Kids can be paid via W-2 for legitimate work (yard work, cleaning, etc.), avoiding FICA taxes if under 18 and they are the biological/legal child of all LLC owners (a multi-member LLC with a step-child situation would disqualify this).
Best practice: use a payroll company to move funds from the STR account to a custodial account, with timesheets kept as documentation.

Other Deduction Levers Mentioned

Augusta Rule (renting your home to your S-corp for ≤14 days/year) — works well specifically for S-corps.
Cash balance/defined benefit plans — flagged as a long-term commitment (multi-year contributions), not ideal for unstable/single-income situations.
Standard STR deductions reviewed: mileage, phone/internet %, professional fees, mastermind dues, hosting fees, mortgage interest/insurance, marketing/photography costs. Home office deduction is generally moot on properties running at a loss (no income to offset).

Administrative Notes

Firm is transitioning communications to TaxDome and text instead of email, for security/encryption reasons.
One advisor has left the firm; existing clients redirected to Kevin or Mason.
9/15 deadline (partnerships/S-corps) was top of mind; 10/15 extension deadline next on the horizon.

Thank you all for joining!

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Friday Weekly Q&A Call - 09/11/2026