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Those specials mostly existed to showcase Mega Evolutions before Ash could realistically battle them (Korrina's Mega Lucario was a novice). I could see one special this time, followed by a time travel arc with Ash and Go. I'd like to see Ash's Quilava evolve during such an arc (no, we don't need...

They won't do anything all that special for the remakes aside from more Sinnoh episodes than usual. I could see a time travel arc for Legends promotion (akin to the Darkest Day one). I think feudal Dawn has a better chance of showing up than Dawn does, since she seems to have something in common...