Key Takeaways: Tax Strategy 365 Q&A
Year-End Planning
Maximize your existing STR
- Improvements and furnishings not captured last year go on this year’s return. They can be added to the depreciation schedule and accelerated.
- Track mileage to and from the property, and keep a log in case of an audit.
Vehicle purchase (Section 179 / bonus depreciation)
- If the vehicle is used more than 50% for business or rental activity, the purchase can be written off whether financed or paid in cash.
- Vehicles over 6,000 lbs (SUVs, trucks) have no cap on the accelerated deduction when used 100% for business.
- Lighter vehicles (sedans) face a cap of about $21,000 this year.
Hire your kids
- Kids aged 9-10 and up can do real work (yard work, assembling furniture, errands, data entry) and be paid through a real payroll provider (Gusto or QuickBooks) from the rental account.
- Run payroll before year-end and have the W-2 ready by January 31.
- The earned income lets you open a child Roth IRA (up to $7,500, matched to income earned). The money can also cover sports, clothes, or tuition.
Augusta Rule (IRC §280A(g))
- It’s not too late. Create a meeting agenda, invoice or transfer from the business to your personal account, and keep rentals to 14 days or fewer.
- Do it through an LLC taxed as an S corporation, which pays the primary residence.
Prepay what you can
- Property taxes (some counties offer a ~4% discount for early payment), contractors, and other expenses in a high-income year.
Backdoor Roth
- It gives no deduction, but it moves money into tax-free growth.
- Convert right after contributing so it doesn’t grow in between.
- Watch the pro-rata rule: existing traditional IRA balances make the conversion partially taxable. Consider rolling those into a 401(k) first.
- Work with your advisor.
Tax-loss harvesting
- Sell losers to offset gains. Net losses beyond gains offset up to $3,000 of ordinary income, with the rest carried forward.
- With the recent volatility, it’s a good time to review your brokerage account.
Oil and gas investments
- They can offer a roughly 80-90% non-passive write-off against W-2 or business income, but they are high-risk.
- Example: a $100K investment gives an $80K deduction, about $30K in tax savings at the 37% bracket, but you still put up $100K to get it.
- Don’t let the tax tail wag the dog.
Real Estate Insights
- Long-term rentals generate passive losses, so they often give no deduction unless you hold real estate professional status. Selling or doing a 1031 exchange may be better than holding.
- Buying in this market: You make your money at purchase. Look for the “ugly house on the block” where you can add value immediately. Builders are offering rate buydowns on new construction.
- A 2026 purchase of a non-passive rental like an STR can still be closed and placed in service for acceleration if you move quickly.
- DSCR loans qualify you based on rental income, not personal income. Several members said rates are now competitive with or better than conventional ones. Lenders mentioned: Movement Mortgage and Visio Lending (via The Mortgage Shop).
- Banking for LLCs: Chase was easy to set up for multiple LLCs, and veterans may pay no fees. Wells Fargo often requires high minimum balances.
Cost Segregation
- Get two quotes (for example RE Cost Seg and CSSI). The software differs, so results differ. Pick the better proposal.
- A rapid report is generally used for properties around $500K and below, and an engineered report for $1M and above.
- Condos have little or no land value, which means more depreciable building basis. Make sure the engineer treats it as a condo, not a townhome. One member had to have a report corrected.
Material Participation
- You must meet the hour requirement every year you want losses to offset W-2 income (typically 100+ hours and more than anyone else).
- Keep a time log, and track revenue and expenses with a solid system (REI Hub, Baselane, QuickBooks, or Excel).
Legislative Outlook
- 100% bonus depreciation is now permanent, with no sunset. It applies to qualifying property, vehicles, and equipment.
- Tax law changes are expected to be unlikely in the near term due to a divided Congress.
Entity Structure and Money Flow
- Members were unclear on how money should flow between LLCs, a holding company, a management company, and a living trust. STR Law Guys advises not letting funds sit in the holding company and moving them on to the trust.
- This needs one-on-one review. The asset protection class next Friday will cover it, and members suggested bringing in an asset protection attorney.
General Mindset
- Buy for the business case, not the deduction. Tax savings come from spending money, so the investment has to make sense on its own.
- The best time to buy is when others aren’t. Incentives like rate buydowns create opportunities in soft markets.
- Documentation wins. Time logs, mileage logs, invoices, agendas, and clean books are what make deductions hold up.
- Plan before December 31. Payroll, purchases, and prepayments need to happen within the tax year.
- Compare before committing. Get multiple quotes, lenders, and opinions.
- Stay calm in volatility. Use it to harvest losses and clean up your portfolio, not to panic.
- Get professional guidance. Entity flows, pro-rata, and Roth conversions depend on your situation, so verify with your CPA or advisor. This session is educational and not personalized tax advice.
Thank you all for joining!