If you are serious, check out Panama and Colombia. I love Costa Rica, but relative to those other countries, it is MUCH more expensive to live there. I would recomend the Dominican Republic, but their infrastructure is shit. Also, I am assuming that you are making a decent amount of money through online ventures. If not, you may want to reconsider moving to another country like the one's mentioned above, expecting to find a job simply because you are American, and planning on opening a sports bar IS NOT an original idea.
. Every time I'm in Latin America, ESPECIALLY Costa Rica, I meet some broke American who moved down there expecting to live like a king, and instead is sharing some rundown shack with another foreigner, while trying to figure out ways to hustle enough money to by a $2 Tico breakfast.
In addition, please learn the fucking language of whatever country you chose to move to. I always cringe when I meet gringos who have been living in Latin America for 5-10+ years and can't speak more than 5 words of the language. My personal opinion, for an american making a middleclass or upper-middleclass salary online, Latin America is one of the best values out there. I have heard good things about South East Asia, but haven't been there yet.