xxxxx2. yyyyetc...I'll give you a possible plan (and it probably won't involve eating lunch with anyone).Good Luck!

Since you owned the property since 1997, you have likely depreciated a majority of these properties and the gain on unrecaptured property (top tax rate of 25%) will really eat up your proceeds.

Boone has a lot of restaurants and some "nightlife" , Banner Elk and Blowing Rock are much smaller but do have some places to eat.  

Aside from that, for investing purposes, look at areas with generally lower property taxes as they can eat into your budget.

They have the full strength of the Govt behind them, and they will wear you down, put you off, delay you, and make you want to eat your shoes after walking thru a cow pasture vs. deal with them.I have heard some folks says they do okay with Section 8, and that is all depends on the local director. 

They don't need to have a physical office in the area (that just eats into your revenue because in the end, clients are the ones paying for their offices/desk workers/utilities, etc).

Your time and maintenance costs will quickly eat away at their equity. 

While you are here, you can drive the neighborhoods, go out to eat at different locations, find where you are comfortable, and search for a property to buy in that neighborhood.

For my job(s) - I plan to first just get a little job whilst in college, after I turn 18, invest in a bike, continue that job and work for Uber Eats (which according to google is 8-12 an hour) so I’ll have a consistent job and a side hustle.

The unexpected, unaccounted for expenses will eat into your cash flow.