A small example is a case in point. For decades there has been the running joke of Kirk making it with all the chicks and particularly the green skinned alien ones. And yet nowhere in the series does this actually happen. The one green skinned alien female he does encounter is nutso and intent on killing him an understandably he wants nothing to do with her. And yet this unsubstantiated cliche was played to for the general audience.
NuKirk was played in a way that affirms erroneous assumptions of TOS Kirk and in extant indicting the TOS Kirk as outdated and not worthy of appreciation.
Now the details don't really matter in a reboot because what happened before doesn't really count anymore. But from the get-go the TOS Kirk was a character to be admired and he would be shown to be worthy of appreciation and respect even with his character flaws. But the end result for NuKirk is not a character worthy of respect and admiration but a cocky, mouthy brat who gets lucky and doesn't earn the things handed to him.
You have really hit the nail on the head. It bothers me that Kirk became known merely as the arrogant, rule-breaking, won't accept the no-win-scenario womanizer. I don't care if that's what people like about him, but it's not an accurate characterization of the man written and acted in the original series. Kirk was a no-nonsense guy who always cut to the point. He wasn't arrogant nor smug nor foolish. He was confident because he was doing what was his purpose to do. Kirk was not the exception to every rule, he had to control himself and be a model of personal discipline to his crew. He loved his ship and being Captain. He once said he had trained his whole life for the kind of split second decisions and crisis that a starship commander faced. He was responsible for hundreds of lives and the seriousness of that responsibility weighed on him. He had a sense of humor, he enjoyed the company and counsel of his officers, and he happened to establish frequent romantic relationships on his travels.