Oh yes, I definitely think Jason would have felt a huge change at entering Bruce's world--and I don't know how much Bruce would have understood it. He would no doubt have recognized it, since it's not like he's blind, but I like it when the comics remind us that Bruce's life really is rare. It's like the person who once commented that Batman has two modes: a butler preparing your clothes and food and dropped into the rain forest with a rusty spoon and nothing else. There's a lot about life in different backgrounds he just wouldn't get.
And it would be interesting if that could lead him to see Dick and Jason as more alike than they actually were.
It is interesting to wonder if he's not most comfortable in that area with Tim.
It's convenient that of the three Robins created in times when verisimilitude or character psychology became much of an issue, the only one to receive that gift is the rich one.
Yes--Jason was created to be different, presumably. He'd been too much of a Dick clone and they were obviously trying out a bad boy idea. I know with Tim there were comments where the were going the opposite way, making him more like Bruce, being rich and educated. While Steph's motivation was more about her father. Though it's interesting to imagine if Steph was a high-class girl whose father was a big time criminal, how she would have been different, even if a lot of things were the same. I could still imagine her having problems, but it would probably be different. Could have been interesting.