I think the reason Silvana isn't included in the Issue 9 cover is because she's technically a villain and this cover is meant to show the good guys anyway.
I think the schools in CWCville is situated as an entire consolidated complex of sorts, with primary, middle and high schools within the vicinity, if that's what we're suppose to figure out from this. The university is probably a junior college anyway. I thought of this place I know just up in Michigan...https://en.wikipedia.org/wiki/Mason_Consolidated_Schools
The Barbara/Robert dolls are named after Chris' parents. The use of dolls the way they appear to be using in this class reminded more of the use of flour sacks as babies in a parenting class.
Layla Flaffy, much like Megagi and Jiggliami, is another fan-submitted character, who's name was originally "Luckette", but Chris, being who he is, wouldn't leave well enough alone (as we seen with Simonla).
Simonla's username is a reference to the video game "Dig Dug", if you didn't notice.
Also, yes, what the f--k is wrong with Chris?