I will as well, that's part of my main and sole playthrough.
I do however have a save file with the boarding school because I'm curious to see if there's going to be a side story between Amber & Dylan and to see what reactions Sophia could have about it, will she be jealous? will she find out that she feels something different and more for Dylan when looking at him with Amber? That's the
ONLY reason I have for a "diverged" save file of the boarding school, it isn't my main playthrough between Mother & Son. If nothing of that happens then I'll just delete those save files hehehe.
The self-defense lesson is the one I mainly have in hope that he'll be able to beat up Aiden later on and protecting his beloved mother.


He seems to just get himself in trouble that Sophia has to fix...
1.- The "trouble" with Bennet and his grade are because he wasn't even aware there will be a test, Bennet mentioned the text while The Parkers were arriving in San Alejo, he wasn't yet at school when than warning was issued by Bennet about the exam, so Dylan didn't have the proper time to study and pass the exam. Also, when Sophia looked at the exam she said that it would be at least a C or a passing grade not for the grade he got.
Bennet failed Dylan on purpose after he met Sophia and found out that Dylan is her son so he is using the "failing grade" in order to coerce or force Sophia to have sex with him. Dylan didn't get himself into trouble there, Bennet took advantage of the relationship and the test and that Dylan wasn't aware there was going to be one to fail him and use him as leverage with Sophia.
2) The "trouble" with Aiden is that Dylan (and Zac) saw how Aiden was bullying a weaker kid, so Dylan stepped up to defend him, maybe he didn't know that Aiden's connections went that far, granted, but he did it out of honor to defend the weak from a bully. Maybe he wasn't comfortable to just walk by and let Aiden continue having his fun. So once Aiden knew Dylan was Sophia's son, he started bullying him to blackmail Sophia to do things for him or he'll keep bullying Dylan because we all know how hot Sophia is so he wanted to see more of Sophia getting humiliated, expose her sexy body to the class and have his fun with a hot teacher.
The only "trouble" Dylan got into was because he wanted to defend someone, perhaps cowards would just walk by but others would step up to defend a weak from abuse.
Even when she has said that back then about the sunbathing, with the bonus side story there's some...potential
(not yet certainty) that Ellie & Dylan could get to see each other naked as I'm sure many would like to see that at the very least, probably that storyline is just to improve their relationship with the possibilities to even get intimate up to a point, and not to make things worse between them.
Anyway, just by theorizing, Ellie has seen Dylan naked, albeit by accident, so maybe, there could possibly be a chance to "balance the scales" and Dylan could get to see Ellie naked too eventually, but who knows?.