That sounds like fun.
My sibling only ever wants to do this to complain - so I don't open these discussions on purpose, because I get annoyed. In some ways, she did have it tougher than me, but not in others, and she never quite grasped that our parents are just PEOPLE, and so yeh, they messed up - sometimes a little, sometimes a lot. You know, like people do. They weren't great - or terrible.
So...the conversations aren't fun and we're both nearly 50, so I think it's past time to stop bitching about how our problems are because of our parents, you know? ; )
My kids are still little (crazy, I know:), so I haven't noticed this. I'll have to try this (in the fun way you describe) with them!