Good lord ser, I'm sitting at just over 15k
If you want really unique vacations, I’d recommend actually traveling a little further away from cities.
But, more specifically, I love Crete in Greece. The south if you’re looking for a romantic getaway - around Matala beach. The northwest, around Chania, if you you’re traveling solo or with friends.
Work: yes, a lot, haha. People (mistakenly) think that travel distracts you from work. In reality it's the opposite. Yes, it's fun to see a new place when you get there. But, there's only so much of this that you can do. I spend most of my time working and find I'm crazy productive considering that I don't have friends, family, etc that distract me from the things I want to work on.
Meeting people: in my experience, it's generally something you have to make a conscious effort to do. You have to get comfortable approaching people. Dating apps, coworking spaces, and Facebook groups help. One of my favorite resources is nomadlist.com.
Safety: As someone who has spent a lot of time in 'dangerous places' (Colombia, Brazil, South Africa, etc) I think it's largely over-rated. But, don't do stupid stuff. Don't be flashy with valuables (an iPhone is a luxury in most places), don't be loud, and don't walk around in new areas looking completely lost. In general, don't draw attention to yourself.
Asking the real questions! Haha, yes, its a pain, to say the least.
Fiat on-ramping has gotten a lot easier. But, off-ramping is still a pain. In my experience, the issue isn't a travel-related one. It has more to do with your nationality and banking infrastructure. If you can off-ramp your crypto to fiat, it's pretty straightforward to spend cash internationally.
Spending crypto for goods and services is becoming more common, especially in places like Argentina and El Salvador. But, it is still mostly a novelty globally.
To be honest, we haven't really faced any problems as a couple from being nomadic. It's important for both people to be excited about the lifestyle and the tradeoffs that come from it. In our case, fortunately, we were on the same page.
I think Thailand is a great first choice. I generally recommend Baliu as the first starting point because of how easy it is to have a social life and find the basics that nomads want (wifi, coworking spots, cafes, gyms, etc), while also having the wow-factor that comes from being in incredible nature. I'm pretty sure all of this can be achieved in Thailand too, but I just haven't had the chance to spend as much time there.
I'd say it really depends on your comfort level with long-term travel. As a first-time nomad, I find Canggu, Bali to be a great pick for these reasons: