. $3k of that might be to establish your new escrow account for taxes and insurance.

It's too short a timespan for a long-term lease on your home, the regulations in Nashville are too strict for you to do a short-term rental; you could do something like a corporate rental/rent to traveling nurses but then you'd need to furnish the house too.  

No keys until they've paid all required funds and established their own utility accounts.

HMLs are a good way to get started for investors and establish a representation.

Has anyone felt the effects of regulations in those states?

5) What, if any, ordinances are being considered (or have passed) regulating STRs?

The only thing that would prevent your father from doing a 1031 is if that property is his primary residence.He can also can indeed use the 1031 to purchase a condo he might like to live in as long as he uses it long enough to establish his intent to hold for investment. 

Assuming regulations allow it in both areas, I'd go beach.

Sister is the only heir and great repour has been established.

@Mo Muigai pay a contractor a few bucks for an estimate on the work unless you have a very established relationship with that contractor.