I have considered this for almost four years. Remote work is really the only option for a US Citizen and it could work for me. During the last four years, I have watched the prices be driven up by US and Canadian citizens and Europeans. I still think that it can be done, but you have to leave the American lifestyle behind.
I have started to look at Panama and Nicaragua or Columbia as options, and I am beginning to move on from Costa Rica. As much as I hate that, it just doesn't seem like a viable option any longer.