I'm gonna be speaking out of my ass for a second here. I honestly think instead of a sequel, there is enough material that I believe having a video series, like 10-20 minute videos, would work out better and you could cover a lot more material without having to cram it all into shorter segments. If you do however make one movie, I would suggest then you explore other facets of Chris other than the LoveQuest, which was the main focus of the first movie. Maybe stuff like "Chris the Entrepreneur," "Chris' Battle of the Sexes," (dealing with his hatred of homosexuals and then his transformation into Tomgirl) "Chris and His Wonderful Toys" (detailing Chris' destructive habit of having to constantly buy toys and vidya, with a running tally of how much money he's spent on it in the last 5 years), "Chris and the Law" .... stuff like that.
Also, I'm making sure I'm coming in at ground level on this one and offer any illustration services I can provide. I'm already doing stuff for DStecks who does Sonichu and bad movie reviews, so something like this would be in my wheelhouse.