I myself am in a similar position looking to acquire a secondary home in the Banner Elk and would plan on using as a STR and would love any input on your findings!!

A couple of follow up questions. 1) After the 1031 exchange, and then after the follow on 721 contribution, I own an interest in a partnership held by the UPREIT.

Even in a best case scenario you would have seasoning issues.

I've been in a similar spot with family.  

Avery Karl has a great book and has another one coming out in a few weeks on STR's.

Lots of investors simply want to go "bold" on all of their projects by using sharp color contrasts, busy tiles that catch your attention, and modern lighting that looks like it belongs in a hotel.

Cleveland is a great market to invest in as well if you're looking for that higher cash-flow.

I guess I could do some work-arounds -- maybe reserve one unit in the first purchase for use as an AirBnb, and reserve my own time in it when needed - instead of claiming it as a primary.Are either of you (or anyone) familiar with a finance product/loan that will allow me to purchase under $150,000 (w/ strong credit) and do much of my own work and live-in a portion as a primary residence?  

@Michael Baum You are right in saying that if guests break $2000 worth of stuff in a year, we have the wrong kind of guests.  

It's best to invest in a company/fund that does this for you.