I have been doing single "main girl" routes + random combinations of side-girls, but i'll have to start more routes soon. with the addition of "suspicion" points banging multiple girls will backfire on us for sure. Especially since we are getting more options to stop/start romances with girls and the option to officially be Jenna's BF.
Still have no clue who the gold digger is. Can be at least 4-5 girls probably, or a combination of girls I suppose. Looking on Jenna's PC was interesting, she knows a ton of stuff we didn't know she knew before.
It would be nice if we could easily see who we are/aren't in a relationship with. With so many girls its hard to keep track of.