How long have you lived this lifestyle?
When we shut down [1] my last company, my girlfriend said "it's now or never." I had realized that I dreaded going to an office every day, so I'm working on making my new company 100% remote.
[1] https://blog.staffjoy.com/staffjoy-is-shutting-down-39f7b5d6...
We're using Earthclass Mail for a mailing address. Works super well. They even cash checks for us.
It is different for Americans, though, they are on the hook for income tax regardless of where in the world they reside.
It works because I am flexible about renting studio apartments or rooms in Airbnb-dorm-like houses, and I don't have other responsibilities or attachments. Compared to the up-front costs, commitments, and assorted bills connected with an annual lease, I prefer it.
We're planning on staying in places for 3 months at a time. It gives us the flexibility to join a gym, take time to relax, and get a routine.
I spent ~2 years as a completely untethered nomad, and love having my feet planted somewhere I love while I still travel+work 3+ weeks at a time regularly so so so much more.
Besides the means (financial) and freedom (remote-friendly employment/relationships) to do this, there are a lot of cultural/social aspects that influence the viability of the long-term nomadism.
1) White privilege: Are you white? Being a nomad is WAY nicer! People are nice and welcoming to you almost everywhere, and go out of their way to involve you in their local stuff, making life more interesting and fun. Also, everyone wants to bang you, if you're into that. Otherwise, get ready to lead a lonely life, struggling to build deeper connections, and having a hard time experiencing the "serendipity of traveling".
2) Your support network's relationship with this lifestyle: This is a romanticized lifestyle for the western world, whereas it's treated as a vagabond-like, evasion of responsibility in Asian culture. This can be draining if your family is mostly disparaging of your lifestyle choice (or others are of your parents for bringing you up wrong etc).
3) You always have a home when you want it: There is a place where you feel safe, you belong, you love and can easily go back to and stay whenever you want for however long you want to recharge in between. If you end up nomading to someplace that doesn't work for you, you can bail on short notice and re-plan. If something happens or if you need to just take a break from the nomadism, you know where to go. If you don't have this (you don't care for your hometown, or was in my case, you have/had legal visa complications preventing you from "calling where you wanted to stay home"), being a nomad can be stressful and uncertain.
As a brown entrepreneur raised in Asia who wanted to settle in the Bay, and chose the nomad life while waiting for my visa to come through, I learned the above the hard way.