I know that the appraisal may work to my advantage as well if they flag it.

I know the numbers well in this market.

I have only done new turnkey builds in SWFL and a couple in Central so no advice on flips or wholesaling in FL but I'm interested in expanding my knowledge as well.

If this is part of their home there will be some expenses that are split with the rental as well. 

For many you are running full speed into a storm that you are not looking ahead at the clouds and unfortunately for those its not going to end well. 

I am definitely looking at the DST option as well.

This seems like a costly fix, as well as a rental safety concern- The basement leaks, the basement is below ground and built into a hill, and there is always stagnant water in certain spots of the basement floor regardless of amount of rain, which only makes it worse.

Depends on the neighborhood as well.

Also if they use house hacking they would have the other tenant that's paying rent would also be technically paying half of the mortgage as well.

With such strong credit, the interest rate should be well below the 8.00% quoted.