The problem was that by the time Bruce realized being Robin was hurting Jason, he couldn't tell Jason to stop being Robin without killing all the trust that remained between them. Taking Robin away from Jason after Garzonas would've damaged their relationship a lot, perhaps beyond repair, and I understand why Bruce wouldn't do it - especially when even after asking other people for their opinion (Babs at least), he still didn't have any clear answer one way or the other.
I think by that stage Bruce must've been scared that if he took Robin away from Jason, Jason would leave. Unlike Dick, Jason never ran away, but after Dick, that possibility must have been clear in Bruce's mind.
Jason was coming from a totally different background. One that maybe Bruce overreached by thinking he understood, in fact. Yes- Bruce doesn't have any idea what it means to be poor. And really, I wish there were more writers willing to remember the class issues at work there than just Winick.