Two questions for the group in celebration of tax holiday cheer.1.

But second, you’re also making your tax free gain, taxable.

Sort of.When a lender agrees to a DIL, they will own the property subject to all other loans, liens, possible lawsuits, and taxes due.

There is of course taking into account the area and if it is getting some life pumped back into it, sure you might have a builder or buyer wanting to put a house on it.I would love to hear from anyone with experience on holding on to an empty lot and just taking the hit on the taxes until you can sell for a large price. 

The second guy was a real-estate professional from Australia who had invested with Ohio Cashflow about a year prior.

Assuming that minimum, I would only be spending about $250 a month on average, which comes out to $3,000 a year, with $27,000 left over (or 25,500 after taxes, assuming I contribute about $5,000 to an IRA that year, which I full intend on doing) for the above. 

Is your DSCR ratio greater than 1-meaning are you cash flowing (according to the lender's criteria of mortgage, property taxes and insurance (and HOA) if applicable).

I presume it would be advantageous for my in-laws to pay back that $250,000 in multi-year installments to limit their capital gains tax liability? 

I could get behind you taking on a live in flip because the downside risk is fairly limited (it's a place for you to live if things go sideways, and you can take 2 years to slowly do all the work and reap the tax free gain).The way that you get killed in real estate is by running out of cash and/or being a forced seller.

A great thing about rentals in warmer locations is the tax write off abilities.