Jason lived (most of) his teen years with Bruce.
This meant that he slowly started to rely more on Alfred to pick him up from school, and stopped using public transport. This also meant that despite being street smart, he started becoming dependent on Bruce’s money.
So a 14 year old Jason would catch himself doing things he never did before (ie. pay for his classmate’s meal without checking how much he had left, buy expensive sneakers without batting an eye or thinking twice) and he’d silently freak out after walking away when he realized what he had done.
This also meant that he had to relearn his independence, in a way, when he was resurrected and came back to Gotham.
Sure, he was a criminal, but he was so used to paying for things without batting an eye that he forgot to check his balance, and suddenly he was eating ice soup in one of his hideouts in the middle of a cold month in November.
So when he was on neutral terms with Bruce and the rest of the family again and he had money, he had to, once again, learn to not be too wary of how much he spent, as he realized he was constantly guarding his food and getting unnecessarily angry when he had to replace something he had bought before.
And once he FINALLY felt secure again, Bruce had his financial downfall and the whole family had to be somewhat more frugal, surviving on savings and a smaller budget. Jason felt annoyed, it felt as though the world was playing a joke on him, and he wasn’t laughing.
It was basically this over and over again:
