A big downside to Rutland is that it is isolated, the closest interstate is an hour to the East that you must take 35-50 mph roads to get there through small towns. 45 minutes to the West is Lake George area which is a hot spot for shopping and outdoor fun things to do since a lot of NYC people visit the area.Crime isn't an issue where I am living but certain parts downtown does have more crime relative to the rest of Vermont.

My belief is that this isn’t isolated to just the smokies, but given the large market here, we are the bell-weather for the STR market.

I always replace toilets, shut off valves, water fixtures, add frostproof water spigots with additional isolation valves for winterizing, switches, light fixtures, Add ceiling fans to every bedroom, GFCI outlets, regular outlets, smoke detectors with 10-year or hard-wired-in, use a quality one coat semi-gloss paint, basic white washer/dryer and Exterior door locks with touchpads (key free). 

Or am I SOL..?

And residents are not isolated in separate apartments but in a private home with bedrooms.

I understand the qualification criteria for REPS but have a slightly unique situation that I haven't found any answers for by searching...99% of my income is from my insurance agency that I solely own.

My concern is that both have very small populations and are geographically isolated from Kansas City.

Lastly, I would stay within a STR city that is primarily driven by tourist income rather than an isolated small town that would be equipped with local laws limiting your STR rental ability. 

Jacksonville like many other cities has some higher crime areas and are not isolated by zip codes more so than neighborhood.

By installing submeters you'll be able to identify and isolate leaks quicker and easier.