It is not about the boob quest per se, it is about having had the date with Sarah on Saturday where she take you to the strip club. That date option is triggered though by start of Sarah getting bigger boob quest and hard stops strip club from foreclosing before date completed if it is active. This also leads to the option of having Sarah come over to company on a Saturday and offer option with threesome Sarah next Saturday, that threesome with whoever you choose will unlock Naomi as an interactable NPC a few weeks later. (When Naomi comes to apologize take the more corrupt options.)
Unfortunately there are more requirements for strip club to foreclose like money, I think knowing and having seen Gaby stripping in the club, likely now also some level for Starbuck (not sure about this) and then there is also of course good old RNG that can eff you over or other events with priority firing over the event of the strip club closing. As far as I know (which is definitely not that much coding wise) the strip club closing is not hard coded to happen but has a random chance to happen and competes with other events that can happen, so if have set in settings random events can happen over 50% that might stop the strip club closing from firing since those other events take precedence. If last is the case setting events firing in morning and afternoon to 0 for a day and then to max 30% should resolve the issue hopefully, but RNG being RNG you can always be an unlucky outlier and it can take forever just as with any other event partially depending on RNG like getting the bright idea to renovate your room. ( If I am wrong bout this last hope someone like
Elkrose who knows way more about the code will correct my answer

)