The down payment size could also impact the interest rate.If you are planning on purchasing property that will need repairs, you will need to have enough capital to do the repairs.Note: This information is for educational and informational purposes only and does not constitute legal, tax, financial, or investment advice.

Zoning, Licensing, and Regulations:-Have you encountered regulatory headaches (zoning, health codes, etc.) that impacted your park’s value or operations? 

Part and parcel, every staudent has access to me via my cell phone number, as you, Ryan, can attest to...Well, while this was a non issue with 50 students, now days being on call like this is impacting my life in ways that are not sustainable at $295.That said, the price is going up as of July 1st.

I wonder if I could get more use from the cash by acquiring another investment property, that I could get forced value via renovations etc, as well as cash-flow.

Once you are within $100–150 of the market rate, you can revert to smaller increases to ease the impact on your tenant. 

Sounds like you’re navigating a big transition and doing a lot of things right already by planning ahead and speaking with a tax attorneyA few things to consider or ask about when you meet with themCapital Gains Exemption If this was your primary residence for 2 of the past 5 years you may qualify for the Section 121 exclusion which allows you to exclude up to 250K in gains if single or 500K if married filing jointlyCapital Gains Bracket You’re right to look at your taxable income including W2 wages and life insurance proceeds to see where you land The life insurance death benefit itself is generally not taxable but if any of it was interest income it might be Ask the attorney to confirm that partEstimated Taxes If you sell the house and owe tax you may need to make an estimated payment to avoid penalties especially if your W2 job didn’t withhold enough for the yearHealth Insurance and Marketplace Credits Since you’re planning to go on your partner’s plan this may not apply but if for any reason you do end up looking at Marketplace insurance your income level will impact subsidies Ask how your income mix affects thisNew Business Planning Talk about how startup costs might be deducted how to structure the business (LLC S corp etc) and whether making a clean break this year or early next year gives you any tax advantageRetirement Account Planning If you have any traditional retirement accounts and this is a low-income year you might consider a Roth conversion or some other strategy to optimize your tax bracketIt’s totally normal to feel nervous about a big change like this but you’re already doing the most important thing which is planning proactivelyHappy to talk more if you want help organizing the numbers or figuring out what to ask I work with a lot of people going through life and business transitions like this and it’s all about getting the right pieces in place ahead of time

That’s awesome you’re teaching financial literacy too — seriously making an impact while also building your own portfolio.

The decision between buying a true investment property vs. a second home with STR income depends a lot on how you plan to use it—and how much you want the IRS involved in that definition.Here’s a quick breakdown to help you compare: Option 1: Second Home w/ STR IncomeYou stay in the property personally (including friends/family time).You can still rent it out, but personal use impacts tax deductions.If you use it more than 14 days OR more than 10% of total rental days, it’s considered a personal residence with rental activity under IRS rules.Pros:May qualify for second home mortgage rates (usually lower than investment)You get personal use flexibilityCons:Rental-related expenses must be prorated based on personal useLess tax write-off potential (can’t take passive loss deductions unless it qualifies as a business) Option 2: Pure Investment Property (STR Business)You limit or eliminate personal use.The property is treated as a rental business under the IRS.You can write off:DepreciationManagement feesTravel to inspect/manageSupplies, repairs, and morePros:More robust tax benefitsClearer cash flow analysisEasier to grow into multiple unitsCons:No personal use flexibility without triggering IRS reclassificationOften comes with slightly higher lending rates or down payment requirements Where to Start:Talk to a STR-friendly CPA – This is huge.

That's your BRRRR/flip strategy – force appreciation, pull your money out, rinse, repeat.

Even though it's common in the area, if it's not legal, it can lead to serious issues..fines, insurance problems, or even being forced to vacate the unit.