I've had a few conversations with my dad about privilege and the bootstrap idea, and his thinking is verrrry sloooowly changing. He isn't one of those people who's always yelling about hard work and bootstraps and never helping anyone else, but his personal idea of success is very tied to it, I think, and the concept of "it's good to work hard for what you want" was given to us in a pretty simple format when we were little. And I think that's a great thing to learn, sure, but it's so much more complicated than that as we know.
It's not something I discuss with him often, because we butt heads on it a bit, but I do think he's changing. I wonder what he would try to teach a little kid today.