One of the greatest Raw moments I can remember is Mankind winning what was the WWF title for the first time in 1998. That was fantastic to watch and a really wonderful moment that didn't lose anything being on TV and not on pay-per-view. I even think that it being on Raw was better than it would've been on PPV, not that we'll ever know.
As long as it's a storyline that's been built up well then there's no reason why it wouldn't work.
Ah, I see.... You COULD always change the results about and have the whole buried alive thing never happen? Or, just give him a career ending injury. It's unrealistic but if you don't like him that much, meh.
I know how you feel regarding The Undertaker, he is pretty tough/repetitive to book for, especially as the Deadman.
Personally I'd have a young guy wanting to make an impact target him. If you could put the Deadman on the shelf then you'd create a new threat right off the bat. That or possibly a heel 'Ministry' Taker? Always something I thought would be interesting to book, difficult but different.