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I've personally met overlanders who has travelled the world on a shoe string. Having left home with virtually no money or gear, maybe just a moped, some basic personal items, and s bit of pocket change. Travelling very slowly, working for food and s place to crash, and a few bucks here and there. Some travel indefinitely and have been gone for years. I once met this young German kid who took his classic 50cc Vespa and criss crossed Africa for three years, living mostly off of simple grains.
I've also noticed (and benefited from personally), that if you travel on a piece of unsuitable kit with a large international fan base, clubs and other fans across the planet will go way out of their ways to enable your continued yourney.
Also, I've met plenty of very privileged people from very not do privileged places - some who has been on every continent. None have been overlanders.
There is as has been mentioned, the financial aspect of it - where there are solutions for the most motivated. I'm pretty sure that different communities across the globe would go far in helping an unlikely fellow in all sorts of ways. Sure the financial aspect can to a large extent explain much. I still believe that the geopolitical aspect is the number one reason - many people are simply not allowed to travel as freely.
A community like ours could easily "sponsor" the occasional overlander from say a place like Guinea Bissau or some other unlikely place. Many of us would be happy to offer free room and board, receive mail, serve as a host for visa applications, give them some work to make a few bucks, donate used equipment we can easily part with, fill up their tank, give some provisions, and put some money in their pocket, etc, etc. We would use our connections to help find other Samaritan's along the route.
The really truely difficult bit for many will be the red tape. They could have the funds, but still find it extremely difficult to be able to travel - at least legally.
There used to be s time when western adventures got plenty of sponsors to ve the first to do something or another. The first woman, the youngest guy, the first with a particular means of transport, doing something for a particular cause as a fundraiser, the first doing this or that... Those days are long gone as doing obscure things has been common place - at least in our part of the world.
What got me thinking about all of this was reading about the Ted Simon Foundation here on HU - a foundation set up to help travellers (albeit mostly about getting published, etc) - really great stuff.
What would have been just as great would be a foundation that would help an unlikely overlander to actually be able to do the overlanding bit in the first place, and maybe getting published as part of that solution (to fund their own trip/return and to help those that would follow in their fottsteps). I'm thinking about something like a network of experts in relevant fields, donors/sponsors, as well as a network of Samaritans - spread out across the planet - people and organisations that would come together to give practical aid to a single eligible traveller - ensure their success. A review board could choose which applicants who would become eligible for the foundations aid...
Unrealistic I know, but dreaming is free.
Hopefully we will meet or hear about more and more unlikely overlanders, journeying through our own back yards in a not to distant future.
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