It feels like you are confounding vacations with actual life & work as a nomad. They won't be the same. 'Doing life' is difficult even when one is settled and comfortable with many support systems. Doing it on the road is having to do everything without the comforts and support net and in the long run it will take its toll.

It more looks like you want to do some traveling and take frequent vacations than actually becoming a nomad.