I sure hope so

Perhaps after they finish their Mark of Mastery Exams.

I figured after the exam they'd be back in real world and back to their KH2 selves. > >

would be awesome

It would be cool! But I would like if we could choose who we want to play with, like in BBS.

 

I would choose Riku first, 'cause we never played with him (excluding Chains of Memories)

Would make logical sense.

Most likely after the exam. But they might get new clothes after the exam. New armor and stuff.

My theory is that you start as KH 1 sora and riku and you grow older throughout the game because yen sid said that they would have to reset there ablities and learn to fight properly

Nomura has stated that only part of the game is the Mark of Mastery exam. So I doubt they will be in the Dream Worlds for the whole game. As such the older versions will have to be playable at some point. However one thing to note now, Sora will likely get a new outfit after the exam, because programming the drive forms on top of the combat system already in place wouldnt make sense (also I am fairly sure donald and goofy wont be present in this game, therefore disarming most of his forms anyway.) In addition, Riku's haircut is an actual haircut, its not just shorter as a result of the Dream World. So don't expect him to appear exactly as he appeared in KH2.

I just want them to get some armor, that would be so hectic

the armor and glider would be a nice addition indeed

i think once you reawaken the worlds you'll revisit them as normal Sora and Riku

Riku cuts his hair before he talks to yen sid to go to the world of sleep go see the trailer