Responses
Violet thought he was only keeping her around because of her status as a former princess, which is the closest thing he could have to a noble title. That’s why she thought she wasn’t special. At the end of the story she realizes and decides to gift Winter a port (since gift giving is his love language)

Violet stating "he merely used money to gain my affections like he does with his staff and with his parents, I'm not special" is so insane, because does she not realize that those people are his lifeline, having parents be dependent on your money since you were three apples tall is insanely traumatizing
and paying your staff well so they don't go to a competitor is basically a business strategy because he doesn't have much else anyways in order to make a living
like, that man put her affection in the same category as much needed parental love, and survival arsenal, and she doesn't see how big it is, and dismisses it as "not special". what would be special if not the affections and loyalty he hopes to gain?
obviously, I'm aware that that's why he loves her so. He can feel that she cares about Winter the person, and not Winter's money, but at the same time, it's such a shame.
It's a shame that the author didn't make it so that the reason Violet dislikes him spending on her is because she doesn't want to be part of the people perpetuating his feelings of uselessness. if only Violet understood him, but no, she completely misunderstands him. More than wanting their love to not be tainted by the way he grew up, more than that, she hates the idea of being seen as an investment that never bore fruit. She feels like when he spends on her, he's deluding himself that he'll somehow gain something in return, and since she mentioned his parents, she must understand to a certain extent why his mentality is like that, but it doesn't seem she's ever tried to actually comprehend it. It feels like a sheer and unfortunate coincidence that her aversion towards his spending happens to fit into the thing he needs to feel warmth in his life.
It's like she sees his spending as proof that he doesn't care, but it is actually proof that he cares so much that it eats him up inside- and what a shame that she's yet to understand that