Or Kirk at the beginning of Wrath of Kahn. But to your point, yeah. "Who am I? Why am I here?" However, it might be a self-aware rhetorical question rather than one that comes out of the confused mind of an old man. They already gave us that confused old Picard in All Good Things, and I don't think we need to revisit that. I have to say that I think Admiral Stockdale was also asking a self-aware rhetorical question, and was not as confused as SNL made him look to be.
Yes, exactly. It was a self-deprecating, humorous acknowledgment of the way the media had portrayed him as an unknown, and he opened his statement in the debate with that question to preface his answer to it. Basically, "Who am I, you ask? Let me tell you."
Eh, I think it's too blurry to really say if they are or not. They're clearly Delta and not a solid colour though. I don't think they're cadets. The uniforms seem to be modified from the early Star Trek Online design used in Countdown.
"Star Trek: Picard in Disney's Atlantis - a Stargate crossover event, featuring Jason Momoa!" Um...because she was married? (Have I strongly enough stressed my hatred for this movie on the board, previously? Because I do. I hate it. It's worse than Nemesis, and that's quite a bar to get under.) It wouldn't be exactly what I *want*, mind you, but it might be appropriate and consistent if at this point in his life, Picard is being treated by younger officers and cadets in pretty much the same disrespectful and ignorant way that Scotty was treated in "Relics" by that kid that saw him to his quarters.
My gut feeling is that it was a real timeline. The irumodic syndrome was implanted into Picard by Q so he couldn't go back and tell everything about the future (there's hints with talk about the Romulan government being taken over by Klingons that Romulus was also destroyed, and likely Q would not be allowed to change that via Picard.) As it was, Picard already went back and told as much as he could (Data becoming a Prof, Riker/Worf fight, etc.) This then made changes. My guess is that Data, as a result of what Picard told him, ended up installing his emotions chip at a different time than in the AGT timeline, thus meaning that in AGT the Ent-D was never destroyed (this only happened due to Data becoming afraid of Soran, leading to kidnapping of Geordi and the compromise of engineer)
Rom had a Starfleet uniform made for Nog in anticipation of him being accepted into the academy. Maybe it led to a successful Etsy biz with Garak. The first Ferengi-Cardassian alliance.
The TNG era civilian clothes really were not that great. Why didn't they take their design from Kirk and crew's civilian clothes in Star Trek 3?
80+ year difference, no way would the fashions not be different. And as more planets joined the federation, their ideas of fashion would influence. The problem was more of a lack of time and budget to put enough thought into it.