After searching for more information on the subject, I came across Bigger Pockets and have since become an avid listener of the podcast.

I kinda agree with @Kevin Sobilo, at least in regard to the multitude of questions you are raising - some of them worth of their own separate discussion thread (which you can search for and you'll find plenty of various advice).But here is my 2¢:2.

I was worried about this based on the google searches but have not taken a deep dive into the tax code.

- What size would tenants deem desirable?

Sorry if I am missing it, but how do you search the forum posts? 

The first thing I said to my friend is that it doesn't sound like too bad of an idea but of course get a title search. 

The process has been, to the best of my non-attorney knowledge, paying for a title search and then, when I go to quiet title, listing any name that may have interest in the property via the title search.

(If you have a SUPER patient wife and the desire to do it.) https://www.biggerpockets.com/renewsblog/how-to-use-the-va-loan-to-build-capital-for-real-estate-investing/

Start by searching the forums here for GATLINBURG and you will find lots of advice or peruse the SHORT TERM RENTAL (STR) forum.

Be patient with your first search, it can take time to find a deal and I've found the harder you try to make it happen, the harder it is to find a deal.