Not sure if any of the travelling digital nomad lifestyle stories are even real, people who have managed to fly somewhere usually got stuck there for many months with all the touristy stuff not working and had to live like regular people, rent regular rooms, apartments, houses, shop at regular supermarkets, etc.
This varies by location, but that’s what I’ve always done. I generally skip all touristy activities until the last moment and just enjoy the different environment, food, vibe, people.
Living away from my hometown is advantageous enough.
I personally enjoy the forced minimalism of having to fit my whole life in a car, but I could see that being tough with a family.
I miss seeing my friends in person, but I wasn't able to that very much before leaving, anyway. And several of them are out doing the same thing, so there are opportunities to meet up.
Overall, it's not that different from living in a city long term, so the same things are important: choose your housemates wisely, optimize for the common usage (work, sleep, exercise), and don't pay too much attention to what the internet thinks.
This is likely more expensive than living in Thailand. I can’t afford nomadic living in the US.