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. 

Additional expenses include property management at $142/month, property tax at $1700/year, and other costs like insurance and maintenance.

Trying to determine how much longer I should do my own taxes. 

Tax advantages.

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

Because Baselane was created by real estate investors for real estate investors, the categories align perfectly with your Schedule E you'll need to file when you do your taxes.

Additionally, there could be tax consequences for you, possibly losing your long term capital gains tax treatment. 

Your CPA would then utilize the results of the study to plug into your tax return when filing your taxes.