I don't have a problem with the class issues in there now and then. I don't think it's as bad as the rich kids doing all right and the poor ones doing badly. If you look at everybody they cover most of the spectrum, from Damian the aristocrat, through Bruce the super rich, Tim the almost-super rich, Barbara the middle class cop's kid, Dick's family presumably would have made more money than some in the circus as headliners but his life would have been with the working class in that small circus, I assume, then Steph's lower middle class and Jason was on the street.
I can see subtle ways that writers show them each relating differently to Bruce's wealth and I don't mind Jason bringing it up. I tend to think of it as something Jason retroactively created, like he's clinging to it as part of his personality now in ways he didn't then. It's all a part of defining himself as not-Bruce. I do sometimes not buy the special knowledge he has. I can believe he'd have some, but I can't really buy him as training himself to such a high level after his death.
Re: the class issues determining who did well and who didn't, to me the reason Dick and Tim are believable as the most succesful Robins is that their personalities were designed to make them good students and tireless workers eager to learn what Bruce was teaching at a young age.