Don’t know. He’s likely going to end up as staff if he doesn’t leave.

For Sawa it was lampooning the fact that he retired as a wrestler so any time he came back to the ring he was doing so as a private citizen and not a pro wrestler. Doesn’t have gear anymore so he wrestles in street clothes etc.

For this it looks like a prop comedy gimmick. (Based on the video)

Yeah HHH would definitely do that to someone.

Going totally on assumption here but this gimmick will likely need creativity to work in the briefcase, newspaper, flip phone etc so hopefully they are up to that task.