If I cohost for someone who has the opportunity to do a cost seg/accelerated depreciation on their property - how can I best coordinate with them so that they qualify for their tax benefit? I wanted to put together a proposal for them, and wondered if anyone else here is a cohost and we can connect regarding the best way to structure things so everyone benefits? Thanks!

I'm in the beginning stages of looking at purchasing a business. How does that flow into my overall tax strategy, where there will be a large purchase price and then ongoing payments through an SBA loan?

Link: https://www.skool.com/taxes/classroom/ec6893ee?md=d433f5b5415f4318987e18632a6244cd Here's a summary of the key takeaways from this session: Real Estate Professional (REP) Status - To claim REP status, one spouse typically must give up their W-2 job and focus on real estate full-time. - Requirements: 750+ hours per year in real estate activities (more than any other job), plus 500+ material participation hours on a specific property — all tracked per calendar year, not per month. - REP status only helps if you own long-term rentals (for cost segregation/depreciation losses). It provides no extra benefit for short-term rental (STR) investors, since STR losses aren't subject to the same passive loss limitations. - You don't need a real estate license to qualify — hours worked are what matter. A license only becomes necessary if your state requires one for the specific activity (e.g., selling property). - There are 19 recognized "real property trade or business" categories (realtor, flipper, wholesaler, property manager, developer, etc.) — meaning hours can come from managing your own or even other people's properties. LLCs and Financing - Moving a mortgaged property into a single-member LLC when both spouses are on the loan can trigger lender pushback, since the bank underwrote both borrowers. - If a lender rejects the transfer, options are to revert the deed back to personal names or add both spouses to the LLC (which creates a partnership return/K-1s). - LLCs primarily exist for asset protection and anonymity — not for extra tax deductions. Rental income/expenses are treated the same whether held personally or in an LLC. - Holding company structures (e.g., a Wyoming LLC owning the title to a state-level rental LLC) generally make sense once equity reaches roughly $1–1.5M, not based on number of doors alone. Cost Segregation Strategy - Cost seg accelerates depreciation but doesn't create new value — it pulls forward a future benefit, which gets recaptured (partially or fully) upon sale. - Best used when you expect a large passive gain (e.g., from a syndication K-1) that you want existing passive losses to offset — a "lazy 1031" style strategy. - Not worth doing on a property you plan to sell soon, or on lower-value properties (biggest bonus depreciation benefit tends to show up around $400K+ purchase price). - Passive loss carryforwards should be checked (Form 8582) before deciding whether a new cost seg is even useful.

If someone is potentially leaving a W-2 job with a 3% 401(k) match (balance is now over $1M) to become a partner in a new company with a handful of employees. The company is still being formed, so this is the window to structure things right before the paperwork is finalized. What would you prioritize or ask about in this situation — both for the old 401(k) rollover and for setting up the new company’s retirement plan? They are hoping to stay on track to retire within 10 years and want to avoid tax mistakes or missed opportunities now, while things are still being set up.

if I file an extension under the Safe Harbor rule because last year we got a refund but this year we will likely owe taxes, am I going to owe interest or penalties? I have not submitted all of the paperwork yet from 2025 and I’m still trying to figure out what we might owe i’m trying to find more receipts and deduction opportunities. Do I still have plenty of time or do I need to hurry?