Actually, I've been thinking about this since I first posted and there is one thing about him that kind of bothered me. Not about the character so much as behind the scenes.
Shortly after I started watching it, I found out that Gene Roddenberry's middle name was Wesley so that kind of made me think that Roddenberry based the character on himself. To me, that made the ones where Wesley saved the day seem a little narcissistic and a bit embarrassing to watch.
I think this is a common impression (at least according to a couple of websites I found) but no one here seems to have mentioned it