Link: https://www.skool.com/taxes/classroom/ec6893ee?md=a4d38121a3154979a9f52d04cd5e46be Key Takeaways: 1031 Exchange with a Price Bump - A seller with a $400K rental under a lease-purchase option was asked by the buyer to add $40K to the sale price, financed into the mortgage and returned via escrow to reduce the buyer's cash at closing. - A 1031 exchange is based on the net purchase price (after closing costs), so the bump likely isn't a federal issue on its own. - Fannie/Freddie conventional loans typically cap seller assists at about 6%, so a 10% bump could create underwriting and appraisal problems. Documents should never misrepresent the deal. - The seller was advised to check with the buyer's underwriter and their own 1031 intermediary. - The $30K non-refundable option deposit was treated as prepaid purchase price, and secured vs. unsecured likely doesn't matter. The hosts will research further in the kickoff call. Cost Segregation and Bonus Depreciation - A cost seg can be done after acquisition by filing Form 3115, which typically costs $600 to $1,000. - One attendee was quoted $2,750 for the form, which the hosts said was by far the highest they'd seen. It likely reflected the cost seg itself. - Avoid a cost seg in a low-income year, since deductions are worth more at higher brackets. - If income is low, pair the cost seg with a Roth conversion to absorb the deduction. There's no refund this year, but it saves taxes over a lifetime. - Run a tax projection first (about 2 weeks turnaround) and submit by November 1st for year-end planning. - Referral companies mentioned were RE Cost Seg (10% discount) and CSSI. Short-Term Rental to Long-Term Rental - Trying an STR for one year and switching to long-term if it underperforms is fine, as long as the first year meets the requirements. - Don't flip back and forth annually for tax benefit. A one-time pivot with a real business reason is defensible.

Link: https://www.skool.com/taxes/classroom/ec6893ee?md=5b763541bd6d49fdbd01a592b2d032ae 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.

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.

Link: https://www.skool.com/taxes/classroom/ec6893ee?md=11589b39042b4557a028893b72788b8e 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.

Link: https://www.skool.com/taxes/classroom/ec6893ee?md=a8cfd76d6c564b39acf25a708873155f Identity theft / property theft - Document all stolen/damaged items, repair costs, and pending insurance reimbursement — the unreimbursed portion may be deductible as a business loss on the rental. - Since a SSN and personal documents were stolen: freeze credit with all three bureaus (Equifax, Experian, TransUnion) individually, report the stolen SSN, and get an IRS Identity Protection PIN (IP PIN) via your IRS online account to block fraudulent tax filings. Syndications & passive losses - W-2 earners investing in syndications get essentially no immediate tax benefit — these are passive investments, so losses are suspended ("carried forward") until either (1) the deal fully exits/sells, or (2) you have other passive income to offset them. Stock capital gains don't count as offsetting passive income. - Same rules apply whether you're a W-2 employee, business owner, or contractor. Short-term rental (STR) loophole & material participation - Material participation tests: 100 hours + more than anyone else involved, OR 500 hours (regardless of others' hours). - Mathematically, only one person can qualify under the "100 hours and more than anyone else" test on a single property — if multiple partners want to qualify, others generally need to hit 500 hours. - REPS is generally associated with long-term rentals and does not, by itself, unlock the short-term rental tax benefits; short-term rentals usually depend on material participation. - Grouping multiple STRs together to combine hours requires meeting IRS criteria (e.g., common ownership) — can't group arbitrarily. - STR definition: average guest stay under 7 days. Midterm rental: average stay under 30 days but requires substantial services (like a B&B) to qualify for the loophole — largely irrelevant if you don't provide those services.