I don't know, except for the carousel piece, I feel like his ideas in retrospect (from today) were pretty lousy while his underlings (Peggy, and strangely Pete, among others) often seem to have better ideas. There's this theme throughout the show that Don is not really a part of the young crowd/generation and entirely doesn't get them/dismisses them. He just assumes their ideas stink, mostly on principle of them being young. And yet there's a strong youth movement going on at the time. It's like his pride just won't accept the idea that he's not as cool or relevant as he'd like to be. Perhaps that explains a lot of his posturing and sleeping around. Maybe it makes him feel young, and in control as opposed to someone who though may technically have the power, is quickly losing his grip on American culture.
Just an idea. Obviously there are instances where this isn't true, but in general, I don't think he's as good at advertising as he likes to believe.