My two cents...

Aschleman, this is just my opinion, but with the Vai > Satriani > Van Halen line, I personally would be more inclined to put Satch in the Hendrix line, in front of Stevie Ray. The way I see it, Satch and Hendrix play/played experimental and technically innovative stuff for the sake of musical exploration, where Vai and Van Halen play experimental and technically innovative stuff just for the sake of it. There's also the fact that Satch, like Hendrix, has more of a progressive blues-rock bent, where Vai, like Van Halen (and, for that matter, Ritchie Blackmore), is more influenced by classical music and contemporary pop and rock. But all that style-association stuff is subjective anyway...

On the Van Halen-Hendrix contest, I infinitely prefer Hendrix, not because he had more soul or crafted his songs more carefully, but simply because I love psychedelic bluesy stuff (and I HATE commercial eighties rock :p). Each to their own, and Jimi's style is more my thing than Eddie's - it's as simple as that.

On Dimebag, I don't think he was an inferior player to Satch and Vai at all, just in a different category. He was a hardcore metal guitarist; Satch and Vai are instrumental rock players. It's very hard to compare players across these categories. I've got to say, though, that I much prefer Dime's playing to Eddie's.

Phew! Sorry for the length..