Guess I'm mostly leaning towards Hendersonville because I just like the town.

I just purchased my second out-of-town rental property. 

Most nitty-gritty things are best left up to your attorney, but experience and advice on where to find resources that can help are what this forum built for.

I have a 38 unit property in a smaller town that I am looking at. 

That's my home town too.

I'd suggest getting to know some investors and real estate agents in town to get a good sense of the market.

Real estate is already an extremely litigious realm with serious past accusations of discrimination, and a database like this would lead to a ton of lawsuits against anyone who built it and its customers I can imagine. 

However, we stopped for 2+ years while we built a new house. 

If I'm out and about in town and a tenant let me know a light switch was broken I can have it changed in a few minutes with on-hand stuff.

Tough thing about a duplex is that you lose efficiencies of scale since there are only 2 units to spread the expenses across.Deal 2: First thing, you need to confirm that it's legal to rent out rooms in the town you're considering.