One of the most interesting analyses I ever read of Kirk looked at the many contradictions contained within the character. Personally, I think it's why he has become such an enduring icon. Sure, pop culture has had a good deal of fun with Jimmy boy, but he still speaks to many.
He contained so many contradictions because so many different people were writing for the show and novels, with each of them looking to create something interesting and noteworthy in their script or novel, and that the character became an inconsistent, contradictory, and superhuman. I always felt the womanizing was simply because the writers always just threw in a girl to get ratings and spark interest. Same with the fighting. These overused plot devices became too incorporated into the character and were so very unrealistic.
Also the "greatest captain of all-time" is a big turn off for me. I dislike hero worship and always think "NOBODY is THAT great -- gimme a break". This pattern followed for the spin-off series too. I was so sick of hearing how great Jean-Luc was or Janeway. Guess I prefer more human, flawed characters. I fear this is going to be a big Kirk the Hero worship festival and I will feel like barfing. Lots of people seem to love Godlike/bad-ass Kirk worshiping that it will be the path Trek takes and I will just bow out gracefully.