As much as it was difficult for Lewis, he still got an almost fully paid career with the exception of the fact that his dad paid for the karting side of things.
Also, even though Schumacher's dad was a brick layer, he actually owned a karting track where little Michael and a bit later, Ralf could drive on all day so I would say they were a bit lucky.
I haven't read into DC but I guess according to what you say Mazz, DC had it tough. I definitely know that Damon had a tough time but a point that could be brought up is that he had his dad's name so I'm sure that gave Damon an extra advantage when it came to sponsorship over his rivals.
To be honest, I know that I'm Irish so this may seem a bit biased

but in my opinion, one of the perfect examples of a cliche story of a guy who was no body and had a tough life getting to F1 was Eddie Irvine. He had to work as a mechanic to fund his way into racing and he did and he did race in Ferrari and almost winning the championship in '99. Mind you, as much of a role model he is for his strive to get to F1, he was a playboy who used to go clubbing on the Saturday night before the race so as far as character, perhaps you can't respect him too much but as for his strive to get there, thats quite an admirable quality in his character.