After quite a bit more pondering, I think I’m ready to articulate why this was pissing me off so much.
It’s just that my parents provided me with enough that I can’t play the “Oh, look at me. See how much I’ve accomplished after being so deprived,” card. But they didn’t provide me with enough that I can gloat, playing the “Oh, look at me, born with a silver spoon in my mouth and everything. Begrudge how much I’ve had handed to me,” card either.
I can’t elicit either pity-filled awe or jealousy-filled yearning. I never get to have any fun.
 And trust me, I’ve tried. It’s been shot down with extreme prejudice.