You’ll likely need to look beyond the city limits (in areas that are still close enough to the city to benefit from its local economic tailwinds) if you want to find deals that pencil out.

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. 

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.

It definitely won’t hurt our local market.

I’ve realized I need additional help—someone local, like an assistant.Here’s my idea: I was thinking of purchasing a small piece of property and putting something modest on it, like a single-wide home or a similar small structure.

Have you gone to any local meetups? 

Find a local one.  

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

Medical pros, job relocators, and digital nomads are looking for comfy pads.Join online groups like Furnished Finder, Nomad List, or local Facebook groups.

Just started our own firm investing in and managing property in our relatively new (~5 years now) home in Charleston, SC.Happy to be a resource to anyone and look forward to making quality local connections!