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).

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. 

I then turn over this expense notebook to my CPA so that he can use it to offset my taxes. 2).

Is there an efficient way to find the neighborhoods that have the least taxes?

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. 

The home I helped him purchase 6 years ago is roughly worth ~240k and he owes ~130k. 

Lake County is landlord friendly and the property taxes are low there too!!

Tax advantages.