I went through the same thing with a much newer friend. It makes sense to you and me logically, but I agree that there was a feeling of disconnect that ultimately made me back off. I'd rather help financially facilitate more opportunities to have a good time, but it just always seems to come off as an insult or uncomfortable, no matter how it's handled.

I feel like im grossly overpaid for what I do in comparison to the much more impactful work that they did, making roughly half what I do, so in my eyes it's only fair to view it as more of a group thing where we can contribute relatively equivalent amounts rather than strictly split amounts? You know?