Is living overseas right for you? I have no idea! Only you can answer that question. And you can only answer it by putting your "boots on the ground". You have to go and see for yourself. Plenty of people with something to sell will tell you how wonderful one place or another is and why you should buy some property right now before the price goes up! Don't do it! you have to spend some time to find out. A one or two week vacation will not do it.
My wife and I live in Panama. We love it! Would Panama be a good fit for you? Maybe, maybe not. We've been here two years and enjoy living by the Gulf of Panama but there are things down here that could drive you crazy! Panamanians think traffic laws are just suggestions. When you ask someone when they can do something they may say mañana. If you look up the definition of mañana it says tomorrow but in Panama it really means "not today". Type A personalities may find the lack of efficiency hard to deal with. But if you are easy going or can go with the flow you may love it like we do. The people are friendly and helpful. Political correctness doesn't exist here. I love that myself! Check it out for yourself!