Do you want me to type up anything for Matthew, like a sort of SU form, or are you fine with just what I say? Just in case anybody decides that they can bunny him or something. As for his Pokémon, they can just be whatever people don't want by the time he appears again. I was thinking Poodledy, Pupster (dogs) and a Bug type.
Finally, you've updated the first post! Fanfare etc. I hope this means we can get onto Team Scar soon.
I echo what DOP said about characters being able to do their own thing within cities, not including anything big. I highly doubt Riku, Gloria and Jayde all share the exact same interests and would be happy to do the same thing. Obviously, for Routes etc. they would have to be together, and for Gyms, but otherwise...
But there will be other events aside from the League and Contests, right? Like tournaments to win rare Eggs and ballroom dances and the Seven Stars Restaurant and flower-arranging shows. Well, maybe not the last one. Oh, and Gift Pokémon, like Eevee and the Riolu egg.
Was Leevoat left leering lonely-like in the light of the leaving Trainers? Have you made any headway with that whole situation?
First post update! Haha.