Yep! All these Cassandra "apologizers"
have nothing to go on except for one twinge of conscience when the MC says he loves her while she is executing her plan to fuck him over (if the player goes that route). On the other side of it is everything you detailed... Plus when it comes to Reina we don't get to see her side of the conversation where she didn't hire the MC. The MC did a bit of "uh huh, thank you, okay, bye" and then left. So Reina could have told him a valid reason for not hiring him, she could have given him a BS reason, or just refused to state anything. Regardless, he doesn't have a clue that Cassandra showed up at Reina's office (unless Reina told him), so he really has no reason to want to see Reina or any of the women who work for her again. Beyond dumb porn "my dick needs a pussy" logic.
As to the idea of thanking June for the "chance" or not holding this against her... He was depressed, hopeless, and then June gave him hope and he began thinking he wasn't a useless unemployed nobody... Now he's right back where he was before, he trusted June to help get him out of the mess his life was in and it went nowhere... At least now he has a chance to work on something with Kindra, something to be excited about for the first time in a long time.
I actually hope that digi.b does a little bit of a time jump instead of having the MC immediately get back into contact with everyone. Really want the next installment to not be dumb but not sure I should be optimistic considering the existence of HoI...