Yes, he gains more knowledge about his past from others and not just his mom, Alyvia and Julia but from Viktoria as well. She corrects some of his "twisted memories" too (like the broken arm for example). He has the sense of familiarity when he walks through her neighbourhood and connects some of the dots about his friendship with her when he sees Julia outside of her house. So he gets the memory of their friendship on his own and others give him more perspective and details. He has lucid memories that others help him to understand and some things he learns from others (like the promise for example).
He takes every one of his relationships seriously, even with Mya and there isn't love there yet (it is just lust for now). I never said that MC doesn't take any of this girls seriously. Her trauma is part of what I already mentioned as her family situation because that is where it originally comes from.
There is a positive development with Viktoria when they talk in front of her home. This is when he apologised and forgives her for bullying him. Since then he is trying to fix that friendship and interactions between them are more competitive in nature instead of hateful. This is the only relationship's fall out where the blame is shared on both parties (more on her but Ben has a big responsibility for that as well just like he said to her in this update). The rest seem to be pretty much his own fault even though he blamed everyone else but himself for decades.
The thing about buying stuff was meant to be a joke.
The whole buisness thing is absurd at first glance but she doesn't seem to care to listen to his explanations. It almost comes off as she doesn't care much about what he is doing outside of school and their relationship (yes, she is curious about how Emily's date went and interested in his family overall just like he is in hers). On the other hand, when he mentioned his work to Cathrine she is so interested and wants to hear more. The game in the same scene seems to double down on the differences between the two girls in favor of Cathrine using bored MC doing shopping with Stephi and Cathrine's disinterest in shopping as well.
You are most likely right that my age and experieces influence my view. I would say even more, that my personal bias toward the characters influence that as well. You see, my favorites are Viki and Alyvia. My bias can probably be seen in my posts but Stephi isn't my least favorite even thou it could look like that here. That would be MC's mom and Emily, and I still enjoy the scenes with them.
I have to go through the whole game again definitely. I probably have many memory blanks to fill for this story.
I will end it here. I don't have more to say on this topic for now and I would have to refresh my memory anyway.
Just one more thing not related to that topic: that Emily's video will definitely be seen by someone who isn't supposed to. My bets for now would be either Alyvia or Stephanie.