Well... that did tell me a potential answer to something I've been considering: starting over and going thru each girl's route individually. Guess that's not possible w/ the way story lines are... tangled.normal way
And what you were saying about Lina did trigger a memory of "oh, wait, I think I'm stuck the same way". But I did go thru the gym challenge and haven't finished the getting Alice fired part yet. Kinda got sidetracked on Grace/Jennifer... Oh, on that... one of the art show comments was like "maybe I should ask Grace for help" so I went back and nothing of that sort seems to be popping up in the Grace interactions.
Basically what I figure is this: The game is still in development, so there are bugs to be expected. Also the dev team created so many potential routes that if a programming logic flowchart was made, it'd look something like the London Underground map. So it's extremely likely they forgot about some routes.
I seem to recall a very early version (like 2+ years ago) having an issue if you bought the poker table "too early" that the event wouldn't fire, as they had it set up to go "hint->buy->event" instead of just checking for the item in inventory at the point of the event possibly happening.
At this point, I guess it's a "wait for the next version and hope it fixed something".
Hey! Are you using just one save, or multiple? I've got like 4 pages of saves, b/c I tend to save at every "major sounding" decision point. It'd suck (why I haven't personally done it) but perhaps going back to a save point from "game weeks" earlier might produce a different result.