Everyone seems really hung up on visas, but if you're just looking for new experiences, why worry about settling in somewhere. Stay somewhere as long as whatever the easy visa option is, and then move along. Most countries have 3 month tourist visas (which you get automatically just by showing up in many cases), and some offer 1-year working holiday visas if you're under a certain age. Some will also let you border hop to renew your 3 month visas indefinitely. Don't get hung up on the difficulties, it's very doable if you want to make the leap. For health insurance, you can get travelers insurance which will probably be even cheaper than your normal US insurance unless it's provided by your employer. Having location independent income and seeing the world is a thing. Google perpetual traveler.