I choose this home although not in a large tourist destination, it is the right size city for me to enjoy when I'm ready to stay there more full time.

I think STR's work well for 'destination points' or theme-based venues.

Less popular as compared to cities like Nashville, Destin, Clearwater, etc... where I am also looking.

I have exclusively invested in Destin and Fort Walton Beach to date.

I am not that familiar with the area, however after doing some market research I see the Fort Walton Beach/Destin area as a good one to start. 

@Drake EspenlaubAs noted, your 401(k) is stuck in your employer plan until you change jobs or reach age 59 1/2 while still employed with the company sponsoring the 401(k).If you have both tax-deferred (Traditional) holdings and Roth holdings in your plan, they may or may not have differing rollover destinations. 

Do you have any specific destinations in either country you are looking at?

It's not the destination, because you will get there.

@David Stebner I manage my own vacation rentals in Fort Walton Beach/Destin, FL and also manage a number of properties for others.

Toward the bottom of the list you'll find lower cap rates along with favorable elements like skilled job growth, built-in scarcity and lifestyle destinations.