I don't think it's fair to blame Ian for making her insecure or to imply it was at his request for her to get new boobs. She'll blame him once they break up or when she gets bored and has them removed, but I just don't think it's true. She's already tried to blame shift on him saying the boob job at its core was a "mutual decision" despite saying it was a gift she felt entitled to since he never buys her anything prior. Anisa is fucking unhinged with wild jealousy problems. She has no sense of self and alters her appearance to try and appeal to guys. I doubt Ian asked for it so much as he was a-ok with new boobs to grab and she was trying to be the center of male attention period. She also assumed it would benefit her career and she attributes big tits to femininity herself. I believe her mom also got a boob job, so it's likely a "norm" in her eyes.
Even when they first got together, people were speculating Anisa would milk a tit job out of him because she hated her bust. She used to lie about having had big tits in the past, would draw herself with big tits, she wore a bombshell for a long time and would claim they were real when she wasn't flip-flopping and acting better than other girls for admitting she actually stuffed for entertainment purposes. It's entirely an Anisa problem imo.
The nipple comment from Ian is from a bad unboxing. I can't remember which but can confirm true: he said he likes tits with small areolas and small nipples overall I believe, it was over someone sending him crocheted breast hats. He's talked about or implied preferring boobs in a few videos actually. He is a tiddy man, apparently.
He and Anisa are an unfortunate pair in that sense. She wanted huge tits and he simply agreed because it benefitted him. I don't think he puts down her appearance as much as people think. If anything, I suspect Anisa puts him down a lot based on things she has said and has been caught saying about him. Everything from gross, to fat, to ugly.
He is an absolute creep for enabling her though.