Your CPA should be able to give you a 1 pager that shows taxes paid if you each file separately vs. jointly so you can find the optimal scenario or understand tax impact of the decision.

Each of these can effect revenue as it is important to achieve optimal Pricing (look to optimize the average daily rate (ADR) which is a function of rate and occupancy).

When High LTV Might Still Make SenseYou can justify >80% leverage if the deal itself compensates for it:You’re buying below market value (instant equity).You have a clear value-add plan (light rehab, re-tenanting, rent optimization).You can refinance within 12–18 months after increasing NOI.You maintain strong reserves (6–12 months of expenses).Otherwise, that thin spread between rent and debt service can trap you.🏗️ 3.

With the $ we are buying taco stands, and "optimizing them with ai".....

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

Sometimes Rabbu can be optimistic on occupancy or nightly rates, especially if the property isn’t fully optimized with design, marketing, or management.With $100K down, you’ve got great flexibility.

Proactive tax planning helps you leverage deductions, choose optimal structures, and keep more of what you earn.

MTRs for traveling healthcare pros is a real niche play, especially since you already work in that space and understand the demand.One thing to keep in mind is that in some of these more affordable metro areas, especially in the Midwest and Southeast, you can often find properties that still cash flow as long-term rentals and keep the option open for MTR if you want to optimize.

It’s easy to get swept up in the thrill of sourcing and closing deals, but without a strong foundation in these areas, your growth may be at risk.An effective tax strategy helps you optimize deductions, leverage advantageous tax structures, and retain more of your earnings.

There are actual companies that are good with doing the listing optimization and everything in number two.