bevo98, I have a similar background: my mom raised my brother and me on a high school education, and I worked through all three of my degrees with minimal emotional or moral (and no financial) support. I'm finding that I can see entitlement in my colleagues when they complain about little things; for example, one of my friends in the same field at a different uni expects things to be handed to him. If he interviews for a job, or puts in for a teaching gig and doesn't get it, he is really miffed and confused, as if, "But why didn't I get that? I should have." When we were both on the job market at the same time, he implied that I landed my current TT job because I'm female (he was having trouble getting offers). He grew up in Cupertino, CA, and now that I know more about Cupertino, I can see how it affected him. I really think that socio-economic class does come between us sometimes... we just don't seem to have the same expectations of the world. I definitely see him as entitled and arrogant sometimes, and maybe he sees me as a bit unrefined and not as smart somehow.
I have been amused and annoyed at the assumptions people make about me -- and the disbelief in their voices when I reveal my true background -- based solely upon my physical appearance and current professional position. I'm tall and blond and seem fairly together professionally, so people assume things about me that aren't true. If they knew about my messy personal life, they may be less inclined to dismiss the reality of my upbringing.
I'm tall and blond too, haha! A funny side effect of all of this, is that I am so much better at acting middle-class than everyone else is. In my doctoral program many other students bullied me for coming from a more prestigious Masters's program, even calling me names. If they had any idea about my life experience as a child or in high school...but you can't even go there. What's the point? Oh, they had it hard, too... yeah right!
I think you can recognize privilege in those who assume you are like them, or assume they know who you are, when you know that they are way off. To succeed, I have had to assume others are not like me (or at least consider that they might not be like me) when it comes to socioeconomic and family background. Other people did not need to think this way to succeed. Maybe it's a generosity toward interpersonal difference? Or maybe this is all nonsense!