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iKingRPG

You said you wonder if this season was supposed to be longer. Believe it or not, it was apparently originally supposed to be on two episodes according to the show's creator. Since Season 2 was supposed to be the end of the show, Rebooted was just going to be a 2 episode special, then it got extended multiple times until it got to 8 episodes. Also that's why so many things happened in the first episode, that was supposed to be half the season.

iKingRPG

secondly the two people in the movie theater you asked about (6:50) are supposed to be Kevin and Dan Hageman, who wrote most of the show. they're also in a few other episodes