Decided to try it again, after like a year or two since I first tried it. Im not at the end yet, but from what I can tell there does not seem to be much new content. Most of the quests are already at "End of content for this update" messages with the same stuff I remember from before. So I guess all the new stuff is for characters or quests I didnt see before?
Also, some suggestions for the dev (or maybe for a modder to wants to take it on?):
1: Clean up quest log. Some simple stuff, like strikethrough, or color coding quests that are complete.
2: Maybe a "Current tasks" sidebar you can show in game that lists ONLY the active task for each non-complete quest?
3: Something in the quest list (or above mentioned sidebar) that shows which quest/task can be acted on RIGHT NOW (example, if it is noon, and 3 of your 9 active tasks can be done at noon, have a colored icon on them?)
4: More info/visibility if an action/quest/event you are about to do is a repeat (not needed), so you are not doing stuff you have already completed. I sometimes spend 5 minutes digging through a quest log each time I need to punish someone to see: Do I need to punish her in office? in class? Public or private? No, so I can either choose one nad hold ctrl to skip it, or "let her off" which is bad. So for the buttons [Send her to your office] [Punish her now] [Let her off], if one of them is needed or not yet completed, it could have an (!) next to it, or something.
5: Same thing with Rachels trainee icon on top right. It is always there, even if I have done the action. So I find myself repeating it all the time (holding ctrl) to see if it has changed/updated. Make it clear that it is complete, but repeatable if you wish.
6: Again, same thing, but with girls standing in halls. An icon showing it is new, or not, so you dont repeat if you dont need to.
7: Dorms list, show which buttons have new content. Almost every night, I click through them to see if anything changes.
If you dont like the idea of giving too much hints to the user, maybe make it an option you can disable so only those who want it will see it.
I like the concept of this game, but honestly having to go back to the quest log 10x an hour to find out what is currently needed is a major grind. I keep getting bored reading the questlog and playing something else for a while, then coming back.