I lived in Asia for a few years as a digital nomad of sorts. My only means of income was freelance software development.
It only worked for me because I have excellent discipline, but most expats I met had a lifestyle of: drinking, partying, smoking weed, and not doing everything possible to not have a regular job. The long-term expats (more that 5 years) were a pretty miserable bunch a well.
While this is fun, it's a rude awakening when you have to come back to the real world and actually make a living and you have been left in the dust. I know a few people that had to move back in with their parents because they couldn't find work after their travel experience.
..and involving your kids? A bad idea. Many governments do not offer you the same protections and rights that you have in the USA. It's hard enough with couples, nearly impossible with kids.