The first thing prior to this would be to verify this is a good tenant, check the lease, and confirm with the owner with a payment ledger that they have been paying on time since they have been there. 

He was working full time too, but the excitement (and nerves) of closing on that property had him checking calulations day and night.

I’d recommend confirming the scope of work and checking with the Tennessee Board for Licensing Contractors to determine if a license is needed for your specific project.

I checked out the app for you.

I check to see how the dogs behave with people, ideally also with children, with dogs, and with cats.  

Lesson learned, check your numbers more thoroughly ahead of time and actually do your research.

Yeah make sure to thoroughly conduct background checks on private institutions you lend from.

I do not use a property management service to advertise and have always used Zillow to advertise, previous references, housing records, credit checks etc

Definitely worth checking out.

What you want is an agent with experience who knows how to negotiate, watch your back, navigate difficult situations, understand contracts and law, provides an objective cross-check, etc.