The 6 playable days are spread over several weeks. It does say in text on several occasions, that several days or a week have passed, since the last playable day. But even so, that was still disappointingly short.
As far as her breaking up with her boyfriend, well her not having a job isn't a problem. Because a few days later, she either kills Jimmy and ends up in Prison, leaves New York forever or becomes Jimmy's Toy. Long before she has to worry about money, her circumstances change dramatically.
I think the game makes it pretty clear that Jimmy is now taking care of Jennifer ( she's described as his wife slave, which could perhaps mean that they've gotten married as well).
Jennifer and Laurie are living together in Boston, where Jennifer is finishing off a PHD in Psychology, and Laurie is at college as well ( Jenn's influence has transformed her into an A+ student).
Jennifer, Tim and Laurie are sharing the apartment that Mark gave to Jenn when they split up, it sounds like they have a Friends with Benefits type relationship.
I haven't played all the endings yet, because I started the game again with the mod, a few days ago. I couldn't get to Hope's or the Dean's endings, because the game was bugged, and I started playing the game again, before I reached the end of Paul's content. So I still have a few scenes left to play.
