Will Ash take some of his Pokemon over, as it seems a lot of older Pokemon are represented. Or at least shift them throughout X/Y Saga?
I think he'll just take Pikachu over, as usual, who will, as usual, revert back to Level 5. He may take along a Pokemon that is given a new evolution in Gen 6, like what happened with Aipom. I'm hoping he brings back older Pokemon for that saga's League as well.
Will either Iris or Cilan follow Ash to the new region? Or will he have completely new companions?
Good Arceus, I hope they don't follow him. Maybe Cilan, but definitely not Iris. I'm hopelessly hoping Brock and Misty come back. Or if not, he'll have the first Gym Leader tag along as usual, or for a twist, the game's male protagonist (I call him Xander).
Out of the starters, which do you personally prefer Ash to have or do you wish for him to have more then one?
For some reason, I see Ash with Froakie. He may obtain Chespin second. But Fennekin... I see the main rival having that one.
Personally, I'm hoping for a reboot, in the style of and with all the awesomeness of the anime trailer for B2W2. Ash should get his older, smaller-eyed design back, and not be much of an idiot. Team Rocket should go back to being comic relief, and the theme songs should be awesome and talk about being the best battler again. I also want Ash destroying bikes and evolving his Pokemon again.