Being that there are a myriad of Cost Seg inputs and outputs - many of which are highlighted in Michael's posts - that benefit from your tax accountant's involvement, we always encourage investors to involve their tax pro in the Cost Seg process from the get-go. 

A good property manager is also an option if your husband doesn’t want to deal with tenants directly.Bottom line—yes, it takes some learning and adjusting, but the long-term financial benefits can be worth it.

By attending these events, investors can not only find wholesalers but also build lasting connections that might lead to exclusive off-market opportunities.To maximize the benefits of these meetups, be open about your investment goals and express your interest in off-market deals.

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 tax benefit alone can turn a break-even or slight negative-cash-flow property into a net-positive investment after taxes.In short: yes, it’s still possible, but you may need to shift your expectations on market or cash flow, and factor in total return (including tax savings and appreciation), not just net cash flow.

They’re the ones who would benefit most from a walkthrough-style education.

If you plan to live in the property, you’ll need to use FHA or conventional owner-occupied financing.If you want to house hack, an FHA loan with 3.5% down on a 3–4 unit is a strong option—low down payment, rental income, and depreciation benefits.

House hacking with MTRs (30+ day stays) offers solid tax benefits, depreciation, pro-rata deductions, and no self-employment tax, but lacks the aggressive STR loophole advantages.Key Tax Differences:MTRs are passive (Schedule E); losses can’t offset W-2 income unless you qualify as a Real Estate Professional (REP).STRs (<7 days) allow losses to offset W-2 income if you materially participate, even without REP status.MTRs face fewer IRS red flags, and you still benefit from depreciation and deductions.MTR house hacking is tax-efficient but less powerful than STRs for offsetting active income unless REP rules are met.

Let me know if you have someone in mind that could benefit from this 💪

Buy an undervalued conventional construction house (appreciation will be much more), renovate to rental quality, sign a lease, and scale from there getting all the benefits real estate can provide.