I'm on my 3rd book of the Wizards series which features him (so far have read: the colour of Magic, The Light Fantastic and currently Sourcery) and I have to say that with everything that he's been thru, i think that he gets a raw deal from the other wizards. For example, saying that he's at level 0, when "normal" people actually start at level 1. But then again, i guess, if it wasn't for his character he wouldn't have these adventures -ken
Also, a lot of that is simply parody of role-playing games like Dungeons & Dragons and the systems they use. There are a lot of jokes in the early Discworld books that totally passed me by until I started playing RPGs.
It seems he can't be redeemed,no matter how he tries.Ofcourse,the attitute of "nothing good will EVER happen to me"doesn't help,now does it?
I kind of feel sorry for him as well. He's sort of like Charlie Brown, he'll never get to kick the football. But sometimes it seems he brings some of the crap he endures on himself.
Rincewind has somewhat more sense than Charlie Brown - he knows not to even TRY to kick the football. He is one of life's losers in that he can never get ahead of the game - EXCEPT - his future is so unsure, even DEATH gets confused by it - HE cannot get a reliable reading from Rincewind's lifetimer. I'm not sure if PTerry would ever dare kill off Rincewind - unless it was in a story to be published posthumously - he's been in from the start - rumours have abounded about major characters being killed off - but even Cohen and his Silver Horde were left with a bit of an out, and I'm not sure if Wuffles counts as sufficiently major, since he died somewhere between books (Mr Fusspot might be a replacement).