Overly focusing on your random example, I know, but Kirk showing up to Deep Space Nine without time travel or Q or something would irritate the shit out of me because if it existed at all, it would be Terrok Nor and full of Cardassians, not dabo tables. It just makes no sense within canon as we know it, and I would expect an in-universe explanation and for this to be plot significant.
Re: Yuletide dilemmas