As much as I love Masters EX, I feel like it's sorta deflated my enthusiasm in the whole concept of characters from different mainline games interacting with each other. It used to be almost an impossibility, outside of certain characters that recurred between gens, and that's what was fascinating about it! But now that the door is open for basically anyone to meet and team up, exploring that idea isn't really as exciting as it used to be for me tbh. :')

However... I still think game characters interacting face-to-face with their own anime or manga counterparts would have had so much potential. They may be the "same person", but many of them vary pretty drastically in personality and lead almost completely disparate lives. So it's less a question of "wouldn't it be cool if they interacted?" and more like "how would they interact with each other?".

Compare Dawn as the professor's assistant, Dawn as a Coordinator, and Platinum Berlitz, for example — despite their superficial resemblance, they're all very different people! What aspects would they find in common with each other, and would they get along if they met? Or as another example, what about Blue, Gary, and Green? They may all be from the same hometown but that's really about where the similarities end. Would they be able to empathize with each other and understand one another's choices? Why or why not?

IDK, it's just fun to think about from the lens of character analysis. I'd like to write something more about it one day...