Which of Ash's Pokemon should evolve?
I don't think evolving would've really suited Bulbasaur, Squirtle, or Buizel, so I'm happy with them. I'm undecided on Totodile though. I like its funny, hyperactive personality but if it had evolved it could've added a whole other dimension to it. The Johto starters in general disappointed me a bit actually. I hate Corphish. I never found Corphish to be funny or even remotely interesting, would've preferred Ash get a Mudkip/ something else, but maybe evolving into Crawdaunt could've gone some way to redeeming it, who knows? I'd have liked to have seen Gible evolve, but I doubt it'll happen now. Would've loved Ash to have ended up with a Dewott, Emboar and Serperior by the end of the Unova journeys but I think it might be too late now. As an egg Pokemon, we could probably see Scraggy become Scrafty at some point, Phanpy-to-Donphan-ish. I'd have loved Ash to have got a Seismitoad but again, I think it is too late in the day now. I was also excited for a potential Ash and Trip trade to get Gigalith and Conkeldurr respectively but alas.
Which Pokemon should ash catch?
Again, massive list. First few that come to mind though, I always wanted Ash to catch a Clefairy like Isamu Akai's. Would've been a refreshing alternative to Pikachu, personality wise, and would've also been quite funny. Always a believer in Ash getting the starter Pokemon, so I wish he'd have got a Torchic, Mudkip and Piplup (hate Corphish and Torkoal, like Buizel though). Would've liked Ash to have got a Bagon as well, maybe the one from AG188?