13d • 📸 Recorded Calls
Friday Weekly Q&A Call - 09/25/2026
Key Takeaways
- Q4 is planning season: Review revenue and expenses now and decide which levers to pull before December 31 (another property, business vehicle, Solo 401(k), HSA, pre-tax 401(k)).
- Deadlines: Individual 2025 extended returns are due October 15, so get any cost segregation study done in the next two weeks.
- Accelerate or defer based on your year: If this year has big write-offs (cost seg, bonus depreciation) and next year will be lighter, defer expenses like HOA, accounting, and attorney fees into January and consider pulling income forward.
- Prepay only when this year is the higher-income year: Deductions are most valuable in the year with income to absorb them.
- House hacking works well: Record your move-in date, since depreciation on the personal-use portion stops then.
- Furnish before you move in: Pay for furnishing and renovations beforehand so they're deductible as rental expenses.
- Home sale exclusion: Prior residency still counts toward the two-of-five-years rule.
- Short-term rental conversion: Furniture and items like a sauna qualify for 100% bonus depreciation for 2026 and later.
- Cost seg is borderline under roughly $200K to $250K, and may not make sense if you plan to move back in, due to depreciation recapture.
- STR qualification: You need at least two stays with an average under seven days, plus 100 hours of participation (spouses' hours combine).
- What counts as hours: Hours count from when you're under contract. Furniture assembly, repairs, staging, and bookkeeping count. Travel from your primary home and tax strategy calls don't.
- Documentation: Keep an hours tracker and a ledger. Bank, card, Venmo, and Zelle statements serve as the paper trail.
- Interest: Mortgage and HELOC interest is deductible when used for the rental.
- Passive losses: Losses from long-term rentals carry forward indefinitely.
- Long-term outlook: You don't need to buy a property every year, so stay realistic about what you can manage.
- Real estate professional status: If a household has no W-2 income, a spouse may qualify.
- Trusts: Your attorney and title company handle moving properties into a trust.
- First death: The deceased spouse's share generally gets a step-up in basis and typically needs its own EIN. Review the "upon first death" provision with an experienced real estate attorney.
- Tools: Baseline is a recommended landlord bookkeeping app that tracks by property. Use a separate rental bank account.
- Hiring family: Pay family members through a real payroll service like QuickBooks or Gusto to make the deduction legitimate.
General Mindset
- Plan before year-end, not after.
- Match deductions to income: Sometimes that means accelerating expenses, sometimes deferring.
- Documentation is your protection: Ledgers, statements, and hour logs win audits.
- Don't let the tax tail wag the dog: Never do something purely for the deduction.
- Keep it simple and sustainable.
- Use the right professional for each piece: CPA for tax, attorney for trusts and titles, specialists for cost seg.
Thank you all for joining!
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Friday Weekly Q&A Call - 09/25/2026
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