Friday Weekly Q&A Call - 09/18/2026 · 🏠 Lower Taxes w/ Ryan

Lyn Cueto

20d • 📸 Recorded Calls

Friday Weekly Q&A Call - 09/18/2026

Link: https://www.skool.com/taxes/classroom/ec6893ee?md=6b22b282f348487e876e47ca231b5b2b

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

Firm Updates & Logistics

BudgetDog Tax split: Brennan and BudgetDog Tax are moving to a new interface with new advisors. Kevin, Ryan, Mason, and the team continue as Tax Strategy 365, with the same admins, preparers, and reviewers.
Pricing for former BudgetDog clients: A discount of roughly 20% was mentioned. Request 2027 pricing and engagement letters by opening a thread in TaxDome. Pricing is finalized; the delay was due to the Sept 15 extension deadline.
Services stay the same: Kickoff call, deep-dive calls, check-in calls, an end-of-year tax projection, and unlimited Q&A (in TaxDome or on Friday calls). For hard questions, use TaxDome so Kevin can research first.
Billing questions: Go through TaxDome so the billing team can review.

Starting a New Business

No profit threshold: You don't need to hit a revenue number to deduct expenses. You need a profit motive and good records. Most businesses show tax losses in the first years.
Separate everything: Open a dedicated business bank account and business credit card (no-annual-fee cards recommended). Track in QuickBooks Online (the "gold standard" for businesses, though not for rental properties).
Deductible examples: Software, website, marketing, photographers/videographers, supplies, licenses, professional fees, trainings, masterminds, networking, and AI tools.
Home office: Measure the square footage of the dedicated space. The simplified method caps at 300 sq ft ($5/sq ft = $1,500). It's allowed per business activity, so spouses with separate businesses can each claim one.
Phone/internet: Deduct the business-use percentage (e.g., 40% of $1,000 = $400).
Mileage: 72 cents per mile was quoted in the session. A log isn't required to file but is your audit protection. A reasonable percentage-based estimate is better than nothing.
Losses can offset a spouse's income on a joint return, such as a W-2 job.

Short-Term Rentals (STRs)

Time log: Track material participation hours from day one, including pre-service work: contracts, realtor and title conversations, closing, setup, design, HOA interactions. The target discussed was 100+ hours, and more than anyone else.
Timing for this year: To claim first-year benefits, the property must be placed in service and rented this year (Kevin suggested holiday bookings).
Price point: Over ~$400K is the minimum that makes sense. The depreciation sweet spot is $750K–$1M. Above $2M is rare and harder to rent or resell.
Improvements and furnishings: Furniture, appliances, TVs, flooring, and similar items can be grouped into a cost segregation study and claimed via bonus depreciation. A property that needs more work can offer a larger first-year deduction.
Travel: Flights, car rentals, and rideshares related to the property are deductible. Keep records.
Financing: DSCR loans (~7.3% quoted) keep debt off your personal credit and help with debt-to-income when expanding, while conventional loans are slightly cheaper. Run the numbers on both.
Loan/LLC question: Whether a conventional loan property can move to an LLC or land trust depends on the lender (land trusts are usually more flexible). Confirm with an attorney (Anthony Brister, STR Law Guys).
W-4 strategy: If cost segregation projections are solid, some clients reduce W-2 withholding. Kevin called this an aggressive option.
Market view: Buyers currently have negotiating leverage. Some sellers who bought in 2020-21 are underwater or cash-strapped.

Selling Property & Depreciation Recapture

Recapture happens at sale, at about 25% of accumulated depreciation, on top of capital gains tax (0/15/20% if held over a year).
Holding longer doesn't avoid it. The only way to defer is a 1031 exchange.
Cost segregation followed by a quick sale can create a painful payback. Before accepting an offer, run a projection with your advisor (a worksheet is available) to see your true after-tax walk-away.
Selling? Post it in the Skool community (~1,500 members) and DM members near the property's location.

Filing & Year-End Planning

Q4 tax projection: Review refund status, retirement contributions (401k, HSA, backdoor Roth), planned purchases, and last-minute deductions before year-end.
1099 vs. W-2: A profit and loss statement includes only business (1099) income, not W-2 wages.
Bookkeeping: Review your monthly P&L, watch for revenue misclassified as income, and check owner contributions/draws versus expenses.
IRS delays and fraud flags can happen, especially when a return has an unusual pattern (e.g., a first-ever refund). Verify your identity promptly and be patient.

General Mindset

Plan before you act. Strategy during the year beats scrambling in April.
Documentation is your deduction. Logs, separate accounts, and organized records make write-offs defensible.
Think after-tax. Weigh depreciation recapture, capital gains, and financing before calling a deal a win.
Use your team. Route complex questions through TaxDome for researched answers.

Thank you all for joining!

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Friday Weekly Q&A Call - 09/18/2026