Deleted my last comment because I may have fudged the dates for this whole Aiden situation, so let me try again and see if I've got this right.
- Playable day 9 (in-game day 16, Monday) is the earliest point Sophia can decide to send Dylan to boarding school and not go through with Aiden's blackmail
- Dylan will eventually be taken to the boarding school on playable day 11 (in-game day 18, Wednesday)
- The "comfortable" way to end the Aiden blackmail will be on playable day 13 (in-game day 20, Friday)
- The second option to end it will be on playable day 18 (in-game day 25, Wednesday)
- Aiden has so far set 3 of the 10 tasks and there are still 2 days left in the week before the "comfortable" option
- Sophia can decide to send Dylan to boarding school at any point during this time.
So, it seems we don't have long before the Aiden situation can be resolved via the "comfortable" option, I just hope it's something good. Quitting her job seems like it could be what happens, but I hope not because it would be sad for her to have to do that because of that little shitstain. Could be that she switches classes but then it doesn't really get rid of him, it just puts him somewhere else and he can still harass Dylan and Zac.
Ideally, Sophia will keep her job and Aiden will be the one removed from the equation, but I guess we just have to wait and see.