From there I was able to get into my first SFR, which my wife told me that I could no longer house hack.Along the way I was able to save much more money, and purchase investment properties throughout San Diego, both on my own, and in partnerships/syndications.Without knowing anything about your situation, I would say that buying a condo/townhome to start is going to be the optimal choice for a few reason:1.) riding the equity wave up will help when you make the move to multifamily. 2.)

The right tax planning can preserve more of your rental income, accelerate wealth building, and provide flexibility for future market shifts.Tax-Optimized Strategy:Your low-debt, high-cash-flow model is solid, but moderate leverage could speed up adding the 4 new units.With no W-2, you can likely qualify for REPS, letting depreciation offset all income (track hours carefully — OBBA tightened enforcement).Bonus depreciation is 100% in 2025, a cost seg on each build could front-load in deductions.Capitalize construction costs from your company to boost depreciable basis.Keep rentals in one LLC and your construction company as an S-Corp to reduce self-employment tax and preserve QBI deduction.Watch property tax reassessment and appeal if needed.Plan for depreciation recapture on sale; 1031 rules now have stricter timelines under OBBA.This post does not create a CPA-Client relationship.

But I don't think it is an optimal strategy for your first investment.

In the meantime, I’ve heard some hosts are getting traction by leaning more on direct bookings, optimizing titles/descriptions with fresh keywords, and boosting visibility through social media.

Fortunately, an issue I don't have, so we optimize for max revenue with the lowest possible number of tenants.

.- SEO MarketingAll the best to you!

Quote from @Kate Stoermer: I just did an optimization analysis of a 3 bedroom in Pigeon Forge area in a resort (shared amenities) for a client. 

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

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