Maybe you should have tried playing the update to see the improved character, because you're complaining about a character that doesn't exist anymore.
Letting people skip important content because they don't like a character that doesn't exist anymore, making the story an incoherent mess that they will complain about isn't a "valid choice".
Seems like a writing skill issue tbh. If you can't write content without having an obnoxious character involved, just make a new character with those attributes and make that one not skippable. It's all about how people perceived Oliver, he was a fucktard (seems you forgot about the shitstorm his appearance caused in the first place) and was optionally booted out the picture (valid reasons in my opinion, but hey, some people liked him). Bringing him back is just a slap in the face and it's pretty obvious why. People don't forget and forgive someone, because hey he's a changed man now, he won't be such an asshole again ( if you really wanted him back, you could even write a scene where he has a talk with Laura and MC and apologizes and they "make up" over some drinks and good fun...not retcon him in and immediately have him cross all the boundaries in one go).
His type of character was introduced too early in the story, I'd venture a guess that people would be ok with a new character that is a bit more dominant at his stage, just not the guy that already fucked up. Although his type doesn't mesh at all with a dominant MC, which is why him being optional was valid. On the sub route, Oliver is a stand out character, because it fits with the narrative. Even though you can choose no humiliation in dialogue, I wonder what was in your mind thinking that having the MC either stand outside the room like a dog or not come home at all is not humiliating for a dominant MC...It's not the first time you put yourself in a corner like that, trying to justify a scene that works on all routes.
I made a poll about this. Supporters have made the choice to bring Oliver back. So I brought Oliver back.
So you decided to alienate the patrons that voted against it...it's a bold strategy, let's see how it pans out. I've seen plenty of devs crash and burn when they started catering to one group of people, hope it won't be your case, since I enjoyed your story so far, even though I dislike the Oliver direction.
Since I'm just a pirate, my opinion won't matter, but I wanted to write this up for 2 reasons. One is to genuinely give some feedback/advice and the 2nd is to have my "I told you so" card for later on. If I'm the one in the wrong, no skin off my back...if you are the one being wrong, you'll lose supporters and "money".
All the best to you.