I honestly don’t see how the story portrays Tomoya’s actions as reckless or just youthful foolishness. His actions are instead lionized as both endearing and a sign of character growth. It’s what the first arc of the story is devoted to. It even bears his name and is the reason he goes to such great lengths in future arcs to help others, so it HAS to be a good thing. At the end of his arc, he gets a peaceful ending rather than a calm reprimand. One could argue that the fact his hard work ends up being for nothing is a hint that he might have gone about things foolishly, but I believe the things he fights for passionately are a big reason Tomoyo is endeared to him (After arc) and why she does so much for him in the After arc . The route plays it up as being one of his strongest traits that while he’s not as earnestly nice as Tomoyo, he can work just as hard to help other people, and according to the narrative, in a more rational manner. I do not agree with the way that theme is realized through the story.
Also, I would disagree that Tomoya and Tomoyo are unaware of the tracts their taking in life. The reason they break up is because Tomoya is lead to believe he could never possibly have a good future, and he will only drag Tomoyo on her road to success down. Interestingly enough, Tomoya had been making subtle changes to his lifestyle (at Tomoyo’s behest) so that he could HAVE a chance of accompanying her to wherever she wanted to go. Because, in a way, Tomoyo IS a role-model for Tomoya. She has more strength and composure and initiative than he’ll ever have. This makes him feel guilty that as her boyfriend, he doesn’t compare, so he puts up with her pushiness in hopes of changing that. But her Student Council peer breaks Tomoya’s thin hopes and coerces him to make the decision he does. One could argue that the narrative ultimately agrees with this (ending spoilers) hence why he dies, ultimately saying that they CAN’T be together, but in this Memorial Edition, the ending is happy, and thus this interpretation doesn’t even apply.
Furthermore, although this is Tomoyo’s story, Tomoya is the POV character, and because this is a sequel, his character arc would naturally continue. Because Tomoyo’s ending establishes that he is willing to work hard for her sake, he would once again try to pursue her path so he DOESN’T drag her down. That’s why I conclude him going through cram school would make the most sense. That doesn’t mean he won’t suffer, fall into ruts, and maybe even fail to achieve his ideal ending, but he WOULD make a conceited effort to follow her life path. It would keep them together without her having to “go down” to his level. And what he does in Tomoyo After simply doesn’t meaningfully contribute to that goal.