You're dead on that this has come up before. I wonder if he feels like he was never entitled to any of it and that when I received it that it marked him or anything he could provide as unnecessary. He also mentioned again tonight how much less money he makes than I do, and his voice shook when he said it. I agree with resentment or insecurity or a combination of the two.
I'll have to think of how I can reframe this. I am unsure of how to go about that.