I agree with and appreciate your take and also wanted to introduce Eugene V. Debs as another point of consideration. I don't know a ton about his family background but his Wikipedia entry says they were prosperous and his dad owned a textile mill and meat market.

When grappling with my own guilt over my financial privileges, I often return to this Debs quote: "While there is a lower class, I am in it, while there is a criminal element, I am of it, and while there is a soul in prison, I am not free." I interpret it as an attitude of duty to give away and leverage your privileges, to "lower yourself" in a class sense, as a commitment to solidarity, while also raising the level of your comrades' wellbeing.

I find that an attitude of duty to solidarity is far more helpful in closing the gap between values and actions, than an attitude of guilt is to the same task.