It is one thing to get a judgement and a completely other thing to get actual money.

You also have DSCR that "Does Not" use income - No income, No tax returns and just uses rents to qualify for purchase or cash out refinances.

Here’s a quick example of a Private Money Partner funding opportunity I underwrote recently.The borrower’s exit strategy is to Wrap the property to a homestead buyer.

Considering they are brand new, with a finish out well above and beyond the rest of the neighborhood I don't anticipate "nobody else wanting them" Thanks for your sarcasm, though That wasn't a personal accusation but I see people on here all the time that say "I found this piece of crap house in the hood for $10k, I can buy it and rent it to a Section 8 tenant and make a ton of money right?"

My tax specialist is telling me I owe about $16k in capital gains tax because I had converted the house for commercial use.

I would then plan to use this forced equity (since I plan to buy a fixer upper) to invest in another home.I have been constantly reading to househack right into the MFH, but this may take some time for me to acquire the money and purchasing power.

I am a private money lender. 

Would it make more sense to live in old side and work on it while living there and still make rent on other side while losing out on being able to claim expenses as tax deductible or live in updated side and loose out on rent for about 4-6month(1300/month) but be able to claim all expenses as tax deductible.

Expenses (taxes, insurance, repairs, etc.).

Tax appraiser accidentally removed the husband from title around 2022, HOA then foreclosed (Florida, HOA can foreclose and first mortgage lien will remain in tact).