Oh this is a cool question! Let me think…
Regardless, I think KH2′s opening event should be first. Not knowing who Roxas is and playing as him is definitely important to the feel of the game for KH2.
The Organization is revealed very slowly through KH2. Xemnas is shown about halfway through. Saix is shown a little earlier. Demyx is introduced during your first trip to Olympia. But Xaldin, Luxord, and Xigbar are revealed pretty late in the game. During 358, there is little mystery as to who the characters are. This could be a bad thing because it ruins the mystique. But on the other hand, having a more personal connection to the Org members before meeting them as Sora in KH2 might be cool too…
The other overlaps with KH2 and 358 are the fight at Memory Skyscraper and the explanation from Riku after you beat Saix. Maybe the end of 358 should take place between those two? Then again, seeing the fight in KH2 (Riku’s explanation) and then understanding WHY it happens when you play 358 is half the fun. Like everything clicks into place. So maybe after you beat Saix, finish 358, then do the cutscene with the Encoder and Ansem, then the final battle.
Then you have that last scene with Roxas at the end of KH2 that would really wrap up the 358 feels. Then again, thinking 358 is about Roxas is a huge mistake. It’s all about Xion. So maybe KH2 would be a distraction from what’s important…
Anyway. I don’t see any inherent problems with what you’re suggesting! I think it could break up the monotony of 358 and it could be an interesting way to see the story from two perspectives. My only rules would be 1.) Don’t start 358 until you finish Roxas’s part in KH2 and 2.) Do ~Tears~ and Memory Skyscraper AFTER beating Saix in KH2 and BEFORE leaving Proof of Existence.
Hope this helps! ^_^
<3 KCM
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