>>77049335You're reading way too much into this and trying to make it into something harder than it is.
Jenny
a) is incredibly stupid and simple, it's constantly remarked upon by the characters in the comic, even her friends
b) was a kid who cared a lot more about leaving Karine behind than about the strange new dude mom was currently seeing
so it's not a stretch at all that she didn't make the connection between the sunglassed man driving the moving van that one time all those years ago.
Jenny and Jenna remember their mother's other flings who she brought home and who apparently lived with them for a while and who took all their stuff, who were NOT in a high-profile marriage with someone else and who had to try their best to keep their face hidden. Jennifer and Will could have met when the kids are at school, or maybe at a hotel nearby, I don't know. But definitely after Jenny and Vicky started to be friends I can imagine Will was extra careful about letting Jenny see him, since Jenny could have seen him in a photo of Vicky's or whatever and the whole thing would have been blown out in the open. The comic makes it clear Jenny and Vicky had already been friends for a couple of years at least by the time Willy was, uh, started.
He drove the moving van himself because that's a fun visual clue, it's cool to notice that several years and volumes later. That's it. Or maybe Jennifer demanded it as a proof of his love or Will didn't want to involve any moving men who might blabber, I don't know.
Will could easily have spent nights with Jennifer and just chalked it up to a business trip or whatever at home, that's not a problem. Also you seem to greatly overestimate the intellectual capabilities of both Jenny and her mom, I mean apparently both Jenny and Jenna were birthed for a man who is a total asshole and Jennifer admits it. She may have kept the baby because she hoped it'd eventually pull Will back to her, or because she felt like having another kid.