Yeah, it would need to be people aged appropriately… even Baby Yoda would be older with another thirty years. I agree we need more characters we recognise, but it should be clear they’re present in the scene, rather than flashbacks. Without reshoots, I dunno if you can naturally add them in.
I’d love to deepfake the Clones to look older (current head-canon is the Kaminoans started producing them again), but I don’t know how that tech works. I wouldn’t mind learning it though.
For Baby Yoda… Yoda about the equivalent to 90 when he’s 900 years old, right? So if Baby Yoda is 50 years old, him being 80 years old is the equivalent of going from 5 years old to 8 years old. I could try enlarging him in a rotoscope to make that difference seem more noticeable, but I can’t think of any other approach. Unless we deepfake Yoda’s face onto Baby Yoda and apply a young filter?