Kestra, you are great to have the attitude you have towards money despite having, as you say, a 'priviledged upbringing'.
I have found that unfortunately Son needs a harder lesson. Having doled out money willy nilly when needed and found the use of it being abused, I have cut off pocket money, he gets his college money which I consider enough as it is more 'disposable income' than I have, and if he wants more he will have to find a job, which I am helping him do ~ I'm not totally heartless

but some kids get used to handouts and it spoils them. Just my personal take on it.
It always shocked me in college how many students had an "allowance" from their parents... that makes college life a little easier for the student, I just can't see what that's really teaching them. I understand when parents help, such as when my parents helped to get me a used car, but actually giving college kids an allowance is crazy to me.
Two interesting takes on the issue.
I wonder if there's something in
Kestra's and my own upbringing that stopped us developing bad habits re: money, despite "generously solvent" parents who helped us through early life. I think in my personal case, two factors were important in stopping me become a wastrel, despite having my education paid for and being given a generous amount of money to get me through university:
Firstly, I only had a very minimal amount of pocket money until I started college. Like, enough for a chocolate bar that day, but that's it. But if I actually needed something, my parents paid for it, and they were pretty generous with their treats. I think this made me realise that while I didn't have any money of my own, I did share in the ownership of family wealth. Not having any personal disposable income, combined with easy - but still controlled - access to the family's money forced me to be as protective of
their money, as I was of the few pounds they officially gave me as pocket money. I don't think they deliberately worked out the logic of this, but it was a good strategy to force me to understand both the importance of saving and the principles of money management. I also learnt how to negotiate, since they'd very rarely buy me something if I just threw a wobbly; I always had to create a reasoned argument in order to persuade them. In hindsight, I'm certain that a lot of the time, they'd already decided whether to buy me what I wanted or no, but they still just made me go through the process of effectively applying for the money.
What was definitely deliberate was the second factor: from a very young age, my father would actively try to interest me in money, finance, economics and the like. He'd get me to help balance the chequebook, look over the bank accounts, check over his payslips from work and explain what each part meant, discuss interest rates on savings accounts, how to minimise tax exposure, the merits of different investment funds, how the stock market works, monetary and fiscal policy, etc, etc, etc.
And as I got older, he then let ME decide (while subtly guiding me) the big investment decisions that HE was making that year, so I effectively got to make the decisions and get a "dry run" at how to manage money. I could then follow how the investments that "I'd" made in previous years did by checking the fund prices, keeping an eye on economic news, etc, etc.
So from a young age, I developed a keen interest in "the game" behind money, and how to get the number ticking upwards, while at the same time realising how ephemeral it can be. By learning to treat it as an elegant game/system, it became enjoyable to manage money well.
Whatever the reasons, it's meant that I appreciated how to handle significant income streams
way before I ever had to handle them in real life myself. I think that helped a lot, later on, despite being more or less bankrolled through university. I don't intend to have children, but if I did, I'd want to educate them about the fun of managing money well, in the same way.