I don’t really think this would be possible given the nature of visas. Many countries require you to apply for a visa from your country of residence, not merely the nearest embassy. I guess with infinite funds he could fly back and forth to handle that, but doesn’t seem practical.
Big community of people who motorbike around the world non-stop. It’s definitely possible to prepare beforehand and actually more admin getting a vehicle through borders.
Biking is faster, you can arrange for all visas for 6 months in advance but not for years. Even for 6 months to have them all approved with no gaps requires either a lot of luck or a very strong passport or both.
Yeah, it used to be that you could get a visa from the local embassy of the country you were currently in. These days, not so much. There are a lot more obstacles to long duration travel now--there are not enough long duration travelers for the system to be set up for it.
