I'm becoming something of a Wheaton fan from watching some of his gaming stuff online. It's odd, though, because in appearance and mannerisms he bears a strong resemblance to a guy I used to be friends with for years but no longer am, for various reasons (many of them quite petty, but shit adds up). So it's sort of a love/cringe relationship.
I was only ever a casual Star Trek fan (grew up with TOS, liked TNG and DS9 - up to a point - and frequently rolled my eyes at Voyager) but I never really understood all the Wesley hate. He was a whiny dork, yes, but so were the entire cast of Voyager and half the cast of DS9. The whole Star Trek approach to sci-fi is pretty vanilla to begin with, so it's not like he was out of place.