Agree $800 seems overrpriced for a room, especially since it seems like he is acting as a live in nanny, the lawyer seems out of touch. 

I want to rebuild but the cost will most likely exceed what it’s worth.  

Same w/ the folks down at planning & zoning, they're super helpful. i'm in knoxville so happy to talk property specifics. sounds like a cool play. you'll be fine as an owner occupant and city STR rules.  

It looks likely I'll need a civil engineer which I am looking at now.

There are also additional costs of operating and maintaining an LLC, like separate bank accounts, annual report filings, tax filings, etc.2.

Sounds like you’re trying to google and perform your own heart surgery.  

I would recommend trying all of it out of you are new and then zeroing in on 3-4 that you really like and start to get good at in your market.

These small towns are a niche market like investing in STR or trailer parks.

Find a market or strategy, sounds like youre starting with land.

RI or NH seem like solid options these days as a Boston alternative.