TG, I've really appreciated getting to know you in this forum, you can be counted on to ask the tough questions. The issues you raise in your post are those I have wondered myself...what happens after the novelty wears off and I'm stuck with everyday life? The things I am thinking about:
1) I am easily bored and need to be learning all of the time. How happy will I be without libraries and bookstores? How frustrated will I be that if I'm interested in a new sport, I can't afford to just go out and buy a bunch of gear and try it out?
2) Will I get frustrated with the rain and mud? Right now, I can always put on more clothes and walk the dogs, even in zero degree weather. Will I feel trapped by the nightly rains?
3) Will I regret leaving my aging parents? What happens when their health goes bad?
4) No matter how fluent I try to get, will I miss having good ol' American English conversation?
5) I love the nature and the beaches, but how much time and money will I really have to enjoy them? Perhaps I'll spend less time hiking and beaching than if I live here and vacation in CR.
I'm going to take it real...slow.