Interesting. What do you do? Photograph? Research? Just travel to take in the world? How do you handle to language and cultural problems from region to region?
Language and culture changes are not problems, they're the very reason I travel. Once I learned enough French the West Coast of Africa was great, and English has been enough in virtually every country in the East so far. I need to learn more Swahili.
For Latin America once I learned Spanish I was set for virtually every country I drove through!
And it certainly sounds like a lot more freedom than most, but the country your van is parked in would be your "master" as well as you are subject to their laws and at the mercy of their justice system.
That's how challenging it is to be free of any hierarchy in the modern world.
> you are subject to their laws and at the mercy of their justice system.
While that's true in theory, in practice there is a hell of a lot of freedom here on the ground. It's extremely rare that I don't do something because "it's illegal" - i.e. riding on the top of a truck with no seat belt, riding a motorbike with no helmet, and basically anything else you would want to be doing.
There is a lot of personal freedom in Africa (& Latin America)
Because driving around the world only costs something around $1500 - $2000 USD /mo, any kind of "good" retirement from a first world country is a LOT more than you can ever realistically spend. You bank account will always go up.
If you're in a smaller vehicle like your Jeep I can see it being under $2000/m. The retired people in giant Unimog overland trucks can spend hundreds per month on fuel alone. Maintenance on those trucks is expensive too.
I get around 16-18 mpg in the Jeep (it's heavy). Most Overland trucks I talk to get around 12-14mpg. They are also diesel, which is cheaper in virtually every country in the world. Maintenance can be a thing for sure, but also remember something like a big Merc truck or unimog is designed to go 200k kms easily without any real work done, where-as my Jeep is not nearly that durable.
Remember too, that $/month is almost entirely dependent on how far you drive each month, given that fuel is by far the biggest expense. If you have all the time in the world, you can drive hardly at all and just spend $1000/mo :)
If you stay parked somewhere for a long period of time sure, your costs will be low. But in that case it doesn't matter what you're living in, maintenance costs will be roughly the same.
[edit] However the prices have increased since I last looked. A truck dealership near me used to sell them, but not for $100k+
Your master may be passive and have broad boundaries, but if you cross a boundary, they will become active and enforce their rules upon you. If you are comfortable living within the boundaries your master deems appropriate, then it can feel like there's no master, but in reality it's just the illusion of having no master. But, even the illusion of no master is still pretty impressive in this modern world.