Well, personally I just would have grounded Dylan until his grades improved. Bennett dealt with. If Dylan wants to go to college he's going to have to put in the effort to keep his grades up. With Aiden hopefully Dylan has learnt not to butt in without adequate backup.
Meanwhile, I discovered something curious while I was looking for evidence of what I said about the boarding school, and discovered that there's a significant difference in the phone call to Alyssa depending on if you send Dylan and Zac to the boarding school or not. It appears you may not get the Alyssa event next update if you send Dylan to the boarding school.