Yeah, no canon points make it both interesting and tricky in some regards but I've been having fun with it so far, and you keep record of what they regain so. It's easy as long as you keep your regain list up to date!

Sakura remembers Maze appearing so he kinda showed up in that but he didn't talk. That's the only memory she has that relates to him. I figured esp once Syaoran shows up, they could then regain memories of each other that much quicker bouncing off each other in-game.

idk if Syaoran would be proud or Concerned but Sakura is asking about self defense so people are offering to teach her sword fighting, boxing and staff so far.

.....lbr probably Concerned because as athletic as she is she is also still a klutz. But yeah the sword thing will probably help her regain memories of that with Sword and Rika-chan.