So after thinking about the upcoming chapters, I've come to a realization that, out of all the girls, Sage's path may very well be the most difficult.
With Jill, her route is the most straightforward due to how she's the only one that didn't try to hide much from mc beyond her name (and we understand why due to how she wanted to see if mc liked her for who she was and not her family). When her family does come into play, that may cause a little turmoil, but nothing that'll be too difficult to move past. The only way to fuck that up is if mc start's sleeping around again, which with that being a mostly chick route, is less likely. Even with Tybalt, this route won't be that difficult since Tybalt is hella incompetent.
Bella will have some difficulties due to her husband most likely returning, causing her to have a mental crisis, but after some time, she accepts that her husband abandoned her and she leaves him. This will in turn get fixed within a decent amount of time and lead to Bella no longer having doubts as long as, again, mc doesn't sleep around. The biggest issue with the Bella route is Jill due to how mc and her ended things. If mc and her were romantic and she had feelings for him, she's gonna be extremely heartbroken to the point of feeling anger towards mc and Bella. If the Jill option was locked, than she may feel luke warm towards mc at most and may be more warry towards him, acting like Bella was at the beginning towards mc.
Maya and Josy are gonna be interesting as I theorize having them both date mc (as well as Maya's father becoming more supportive of MC) will lead to more conflict due to the two possibly starting to grow jealous of one another, especially if they get into a fight, forcing mc to have to decide who to spend time with. This could lead to the route where mc will have to try and work to keep them together, or lead to a route where Maya and Josy split and thus force mc to have to end it with one of them. Add in Tommy, and that's make it even more difficult when it comes to Josy.
With Sage, the issue comes from something we saw from her, her paranoia. Sage is gonna be the hardest because there's a good chance she's gonna start acting towards mc the way she was acting towards Chad. Mind you, her paranoia was right with Chad, so her accusations were legit, but she did make them without having any proof, to the point she was freaking out on everyone just based on her thinking Chad was sleeping around behind her back. This is most likely gonna happen again towards MC, ESPECIALLY if he's known for sleeping around prior, to where flirting or other girls flirting with mc may set Sage off. Add in the Jade factor where, if mc and Jade were having an affair, will lead to Jade being extremely vindictive knowing that mc ended things with her for Sage, causing her to probably want to sabotage mc, so she'll be manipulating Sage bad. Then if mc is still sleeping around, will most likely lead to a huge fallout between mc and Sage.