I certainly don't put Sakurai on a pedestal, but I do have honest respect for the man and think he's pretty damn good at what he does,
most of the time. His ability to hold strong with such a stressful position and health issues is also admirable.
I can't say anything about his favoritism regarding Pit being put on the same level as Nintendo's greats. Perhaps he's a little too prideful of his latest non-Smash game, but I'll play the devil's advocate. At least with Kirby, I don't blame him at all for using only his own creations from it. Even if I willingly gave my character to someone else to use, I can't imagine I'd be all that happy with using anything they did instead of my own work. Again, even though he no longer works on it, it's still his creation, so HAL probably doesn't say anything in regards to Kirby out of pure respect.
You raise a good point about the communications, but there's also the matter of Sakurai already having to deal with a large number of outside parties rather than just a single one. I'm playing the devil's advocate again, but I do still think that he never got word on Tropical Freeze until late into development, so he just didn't bother with anything but Returns. In regards to Diddy's animations, Sakurai, or at least
someone on the team, had to have played at least the first DKC.
Just look here, skip to 11:15 if you want the important parts. Diddy was so accurately portrayed that it's not even funny. Maybe he sees them as funny jungle animals, but he still makes it a point to capture some essence of the character.
I can't really give him much else, but I do think he at least
tries to some extent, even if he gives up (Ice Climbers).