I've been through this whole thing. Where I am now is I'm older and living in Thailand with a wife and kid.
When I was younger I had the same big ideas about traveling while earning a living as a single guy; current fashion is to call it being a "nomad". There are more and nicer coworking spaces now but it's still just working during your vacation.
I ended up grinding at a big tech company, saving/investing a lot more than other people who were living it up, and then retired (very) early. I also grew up a little during the process and wanted more than just an ocean view and party life. That happens to most people, although not all as you can see with a trip down Walking Street.
Life in Thailand works for me and my family. No visa runs if you have a spouse or retirement visa. Most modern conveniences are available. Speaking the language with a good accent helps a lot.
But costs are surprisingly high if you want a "normal" life. Cars are way overpriced due to high tarrifs. Electronics are pricey as are many western foods. My kid goes to an international school, which is really the only viable option for education, and that costs about US$10,000 per year. Real estate in the US varies greatly in price, which means someone like me who wants to live away from a city could get a ranch in the southwest US quite cheaply. But in Thailand land prices are kind of high almost everywhere. We have land near Khao Yai National Park about two hours from Bangkok; it's very nice up here.
Long story shorter, life changes a lot as you get older; you want different things. The advice in the article worked for me. If was to do it over again I would be tempted to try the "nomad" life as a freelancer. But knowing what I do now I would probably repeat what I did - work for 20 years at big tech co, take nice annual vacations, save a lot, retire early.