Been there, done that with the visa hopscotch. In Southeast Asia, I'd max out my Thai tourist visa, then bounce to Vietnam for a month, rinse and repeat. What eased my mind was ensuring I paid all local taxes on income earned remotely, which most digital nomads skip. It felt less like gaming the system and more like contributing fairly without overstaying welcome. Setting up a legal entity in one country eventually gave me a proper base, but that took years. The key is transparency with local authorities where possible, even if it's just declaring your funds at immigration.