Jill would be near perfect if she wasn't so damn naive. She thinks the simple solutions are often the better ones cuz it's by the book and the right thing to do. Sometimes the right thing to do is the wrong thing to do, like bringing the MC and Chad into the office after their fight. Even on the DIK path I was like "Man, this isn't how I'd want Chad to lose out, I'm not some snitch." And then there's her getting all emotional after finding out it was the MC and Derek who broke into the mansion during Hell Week. Even if you didn't steal her money she still accuses the MC of stealing her panties even if he claims he didn't, she storms off disappointed like her close friend betrayed her without believing him. Like, what?
Maya and Josy just have way too much baggage. I get their schtick, I get the appeal. But the path itself is a huge commitment because instead of other potential events the game goes "oh yeah, you're on this path, you get to hang out with just these two for this segment".
Bella is one of the nicer ones. Her glare scares my soul though.
Sage is probably the most down to earth ones and her baggage is kinda hanging by her sleeve so it's not overly buried. Oh no, the real baggage is her family. You can also just pick the Single route and get to have guilt-free sex with all the side chicks (and ultimately take Tommy and Derek's advice of being free and without the burden while you can).