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Well, there are some quests that you have to start in order to finish others, but I guess if you're not doing any of them then none of them are prerequisites for continuing to do none of them.

I guess it's true that most of the bugs have to do with specific questlines, and they could theoretically just be incomplete... but if that is the case then they've been left off at an incredibly weird spot rather than a reasonable cutoff point.

Everything that can't be removed. Even without the optional ones, there's always the collar. If you were able to complete it, either there is some way to remove the collar that I'm unaware of, or somehow you were able to complete the Alex questline without removing your collar even though the button is not even clickable for me. It seems very weird that there would be a way to remove the collar without the game immediately ending, because as far as I can tell, the main quest is "find a way to remove your collar." If that is possible and there's more gameplay after that, then I guess there must be another main quest that you only acquire after completing that one?

Okay. So, I looked at the code. The actual issue is that the in-game tooltip describing why the button is unclickable is extremely misleading. It heavily implies that you must not be wearing any clothing at all, which is very much not the case -- you must be wearing clothing, but not any removable bindings. It doesn't actually care about unremovable bindings. So I could not figure out why the fuck it wasn't working, because I was trying to do what the tooltip said to do and not what the actual code of the game asks for. So yeah... that's an ultra misleading tooltip and should definitely be rewritten.

EDIT: Aaand now that I've done all of it... Complete waste of time. Literally did all that and way kinkier stuff with random inmates a billion times, and we're supposed to act like Alex is teaching us something about kink. Also no benefit whatsoever after completing it. What a pointless questline.