And when I speak with people (or write on my blog) I'm always VERY transparent about the unique challenges of the market there.

Is this something you've ever done as an individual landlord, or is this something more for larger multi-family properties only? 

You'll likely find it easy to find people who will tell you what you want to hear, but you really need hard facts not speculation.But for some speculation, if you're talking about the Nantahala River or Little Tennessee, sure I think you might be able to do $22K/yr, but not much more, unless perhaps the places are uniquely styled. 

When you do that groups of people will apply, rather than random individuals.

It recently dawned on me the idea of a non military affiliated individual assuming a VA loan, would this individual be able to then also gain the benefit of using an IRRRL since they have now acquired a VA loan through assumption?

I’m excited to join this platform and connect with like-minded individuals passionate about real estate and investing.

Finding the right market is key since every area has its own unique dynamics.

But he chose that one over the others because it was very user friendly (for our older managers) and it offered a 'Groups' function where we could add certain individuals to different projects.

First thoughts are finding a way for the tenants to use it for a fee, either rent the space monthly or create a space that can be rented on a per-use basis....or possibly rent to another non-tenant individual for office use of some kind. 

STRs have unique tax considerations, so setting up the right systems early will save you headaches down the road!