Quote from @Gregory Wilson: A few things there, Brendan.First, an LLC with you as a member and your (wife, son, pal, etc.) partner as a 1% member will file a Form 1065 which is about one tenth as likely to be audited by the IRS as a Form 1040 with a Schedule E rental activity (which I presume you will attempt to show is an active business).Second, you want an LLC because when your local Alabama handyman drives his girlfriend's uninsured truck into a van load of U of A medical school interns on I-22 when he goes  to get some shingles for your roof, on your business, you don't lose everything you have or ever will have to an uninsured claim. 

Im not an STR SME - I would check with Mike Savage and Dan Rivers - theyre the local experts on STRs.

Nevertheless I am local now and I have that real estate desire (which never went away).

With careful planning and local insights, Richmond can be a solid addition to your investment portfolio.Good luck!

I am a local realtor in the Boone, Blowing Rock, Banner Elk area and would love to help out if you need any assistance.

Find a local one.  

That will give you a good idea of how it will go.Plus you can go over to https://awning.com/airbnb-estimator and put in some addresses and see the local competition.

Definitely stay away from the guru/seminars crowd and stick with the organic communities like BP and local free meetups.

HELOCs on investment properties can be tricky since many traditional banks don’t offer them, but some lenders, and some local credit unions might be worth checking out.

since purchasing the property with a 10% down portfolio loan through a local bank, I have done extensive repair work and renovations.