Quote from @Steve Holt: @Michael Baum Sure feel like an early adopter!

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

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

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

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. 

design one for yourself. think about your market. like in columbus we have infill lots at 30x120 and so we developed and designed a house for ourselves. we build the same house and continue to Make modifications. it's the only new build we offer to build for clients. that's just my opinion. architects we didn't even use we looked at national builder Floorplans and decided. our typical lot is 3000-4000 square feet that we build on 

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

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.  

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.