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).

He's optimizing it, good for him. 

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

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.

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

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.

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

I'm 22 (just getting started with my investing journey) and I'm trying to figure out the most optimized way to allocate my funds, but I'm having a hard time balancing retirement investing with saving for real estate.

TechvestorMashvisorPriceLabs, Wheelhouse, AllTheRooms Analytics, Beyond, Rabbu, and others all offer varying levels of pricing optimization and market benchmarking.

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.