I ask this question because I own a second home (not a rental property), owned for 6 years. I'm in process of my first STR purchase on a property approx 90 miles away from the 2nd home and 77 miles from primary residence. I heard somewhere along the way that there's limitations on the number of 10% down payment home purchases one can have. True or false? Is there anything (IRS, FHA, etc) preventing me from purchasing another home with 10% down? I'd use the property at least 14 days throughout the calendar year which I think is the minimum required usage to be considered a second home. Reason for 10% down is to have as little cash out of pocket as possible for next home purchase. Thx.

Hello! I am looking for some advice on STR insurance. We are converting our old primary residence that we lived in the past six years (we moved out June 2026) into a STR. We still have a home loan through the VA on the property. We currently have homeowners insurance on the property, but understand that we need to update this to reflect additional policies such as loss of income and an umbrella policy. The property will be placed in a single member LLC. My questions are: · Can anyone recommend an insurance company to reach out to about this to set it up? · Does anyone have a recommendation of what policies to get for STR insurance? Perhaps even recommended coverage amounts. · Could converting it to a STR trigger any “payback” of a mortgage loan? Has anyone experienced this? It’s our first time going through this process, so any advice on the insurance side of things is more than welcome. Thank you!

Link: https://www.skool.com/taxes/classroom/ec6893ee?md=ea5a97a26770489a836944eb8d9f13aa Here's a summary of the key takeaways from this session: 1031 exchange into a syndication - Standard LLC syndications do not qualify for a 1031 exchange. - The most viable option is a Delaware Statutory Trust (DST). - You must identify a replacement property within 45 days and close within 180 days. - The full value must roll over — equity, allocated debt, and closing proceeds — not just your original down payment. - It must always be investment-to-investment (not primary residence to investment). Like-kind is flexible: commercial-to-residential and vice versa both qualify. Cost segregation & property improvements - A cost seg study doesn't need to be done in the same year you acquire the property — time it for the year you have the highest taxable income. - Adding improvements after the initial cost seg (e.g. a pool) doesn't require redoing the entire study — they can be added manually to a future return. - Roughly 20–25% of a property can be accelerated via bonus depreciation; the remaining ~80% depreciates over 39 years. - A great rental property hits the trifecta: cash flow, depreciation benefits, and appreciation. - When deciding whether to do the cost seg before or after renovations, doing it after is often more comprehensive, but either can work. 1099s & contractor payments - 1099s are due by January 31 for the prior tax year. - Always collect a W-9 before a contractor starts work — don't pay until you have it. - C-corps and S-corps are generally exempt from receiving 1099s. - Payments via credit card or third-party platforms (like Plastic) typically don't require a 1099 — the payment processor handles reporting. - Zelle is treated as a bank transfer, so 1099s generally still apply. - Use track1099.com to file 1099s easily once you have W-9 info. - In theory, you can't deduct contractor expenses without issuing a 1099 — but enforcement is inconsistent. Do it right regardless.

Little crunch time to get everything to the team by the 7/15 deadline for the extended filings (but got it done!). I was using Wave for my non real estate which was fine albeit all manual … Stessa failed me big time on missing imports etc. I’m considering moving to Xero or QBO… the reviews seemed pretty good on Xero and they are half the price - also have Claude connectors etc. Anyone use them? Also if I’m going to make a shift I might as well better adhere to the format the tax team needs to file - can someone point me to the chart of accounts file that Ryan recommended?

Hey everyone. Happy to join this group. I have a question in regards to whether anyone has experienced an IRS audit on an STR purchase and won where you manage the property remotely and availed yourself to the STR tax loophole in particular to the 100 hour material participation test where no one has done more hours than you. @Ryan Bakke, CPA I believe you mentioned the IRS has come and performed 7 audits on your clients where you have won on all of them. Was anyone managing their property remotely? My CPA believes I would fail the audit if I wasn’t within driving distance to the property and that I would have a hard time demonstrating material participation. I disagreed but was curious to hear other opinions.