If you can find a market thats affordable but within driving distance so you can at least keep an eye on the property I would suggest that before going to another market.

There are lots and lots of information and posts about 1031 exchanges here on the forums.I'd suggest the search function and the 1031 sub-forum and you'll find endless reading/education.

A lot of people suggest not having too many properties in one LLC also.It may vary by state but a UPS mail box that you rent can be used since it is a street address, not a PO Box, and used as the LLC address.

You can also look at each of your AirBnB 'comps' in your area and see if there is a commonality among the property 'hosts' or 'co-hosts', and if there is, I'd suggest you reach out to that person to learn more about your local market.

My properties there have been pretty stable with very little turn over although I would highly suggest doing a thorough tenant selection as with any rental.  

To me, being financially free would to be able to work a more flexible schedule, be on the boat on days when I would typically be at work or on the mountain on mid-week powder days! 

Any design/functional suggestions would be much appreciated!

Again there are a lot of exceptions to my suggestions of what I look for but at least you get one perspective from fellow investor.

I would keep them on a month to month , but suggest a $150 rent increase during your initial call.

I should clarify that I didn't mean to suggest long term gains are't important or worth considering.