I haven't even begun to look for sellers or buys yet.

Some agents do this well, some without a license do it even better.Having a license to serve other clients first and help you conduct your own transactions second is how I would look at it.When analyzing deals I will prioritize sharing with investor clients first and only pursue it for myself if none of them want to purchase it.Happy to talk more as you pursue all of this!

You could do General Contracting where you'd need knowledge of all trades or manage a team of one single trade. 

And this might indeed require some time to pass before doing that.You could still create a single member LLC with either you or your wife as member. 

I recommend you budget 5% of the gross rent (for the whole place, even what the rent would be if you were living in it as a tenant) for repairs and 5% for capital expenditures.

I am always looking for unique items even if I don't need them. 

You ALWAYS need to do your own due diligence and even MLS listed properties may look like a deal on the listing but when you analyze them deeply they are not. 4.

This will free you up to get a loan in the 2 or 3% range... even in 2025! 

Capital gains are calculated as:Sale Price - (Original Purchase Price + Capital Improvements + Selling Costs) - depreciation (if applicable) = Capital GainYour mortgage or HELOC balance does not affect this calculation—it only determines how much cash you take home after the sale.In Massachusetts, if the home was your primary residence for at least 2 out of the last 5 years, you may qualify for the Section 121 Exclusion, allowing you to exclude up to $250,000 (single) or $500,000 (married filing jointly) of the gain from federal capital gains tax.

Quote from @Melanie Baldridge: In 2025 the bonus depreciation rate is 40%.This means that if you bought a property for $1M in 2025, did a cost seg study and found $300K in eligible assets that you could depreciate, you could take 40% of that $300K as bonus depreciation to offset your income in the first year.40% of $300K = $120K.You then apply that $120K to the owner’s personal tax rate to find the final amount that they can defer in year 1.If your tax rate is 37%, you can defer $66.6K.This is a big deal even at the 40% bonus depreciation rate this year.It’s a massive benefit