However, the path of least resistance may lead us down the road that we wish we would have never traveled.  

We also travel several times a year to blues dances and exchanges around the country.

Your appreciation your so confident in might be depreciation rather than appreciation.Either way I wish you best of luck.

-The dream of traveling the world-Never in my wildest dreams would I want to work for 1/3 of my life just to pay for my old age. 

I have traveled the country for the last decade and am proud to call Portland home.

I'm looking more towards major cities so that when I travel, my friends, family, and I have a free place to stay!

@Cecil Russell  Sounds like the issue isn't a "business structure" so much as sounding confident on the phone. 

Choosing a location is based on many factors (for me): proximity to where I live, my confidence in the cashflow, quality of the property (I stay away from fixer-uppers b/c those can suck up your time), and -- so long as I am confident that it will cashflow -- appreciation potential is a nice "icing on the cake". 

I am confident I can get at MINIMUM $650 for the side that I'm not occupying, perhaps even more if I were to rent out the two car garage. 

I am confident that I can answer any of your questions that you may have a long the journey.