I'm finding this thread fascinating and very much applicable to myself. I'll be the first to say that I've had a balls-out-ridiculous-privilaged-life. My parents sent both my sister and I to the best possible schools, and paid for both of our undergrads. While my sister went to a US private college (with the costs that come with it), I instead chose a university back in my father's native Canada. However, since my parents paid for the tuition, room, and board for my sister, they paid for the equivalent of mine (tuition, rent on an apartment that they chose with me - dorms past the first year didn't exist, and a 300$ a month stipend to feed myself). Any entertainment money was made on our own (we both started working at 14 and continued part-time during uni to cover costs of «extras». While the costs for me were significantly lower than for my sister, their promise was that we would come out debt-free, not a set amount of money. I never had any issues with this.
Flash forward a few years: after graduate school (not covered by my parents), my sister moved back in with my parents and lived there rent free for a year. I was never jealous because while I absolutely adore my parents, I wouldn't want to live with them again, simply because as an adult it puts unecessary strain on the relationship in my opinion.
Flash forward a few more years to today: my sister decided to start a farmstead to make cheese. She works damn hard, longer hours than me, and way harder (office life is easy lets be honest). However, instead of having the added stress of a 350,000$ mortgage and 150,00$ business loan for the construction of the cheesemaking facility, my parents bought her the entire farm and paid for the construction. They didn't want her to have the financial stress. And in their words «we can either give it to her now or when we die, and we'd rather give it when she needs it.» None of this makes me jealous for the simple reason that I know that if I were to start my own business, they would help me out as well. I can honestly say that two things with this situation bother me: the fact that my sister was never forced to go through the brutal but important «develop and get a business plan approved by some investment/banking power», and also, I fear that my parents are far too generous for the amount of living they have left. On the first point, my parents are well aware of my feelings, and they are both business saavy people and have assured me that they never would have done this had they not gone over her business plan and believed in it. On the second point: my parents could out-mustache MMM any day of the week, and while they are both scientists never making multi-millions per year, we lived FAR below our means and they have assured me that they will be dead with several million in the bank because they don't know how to spend it.
Whenever my parents come visit me, my mother always wants to go shopping with me, because they help my sister with necessary things. However, I always refuse, because I don't need anything. We actually got into an argument the last time they were here, because I said that whenever they want to buy me something, be it groceries or clothes, I just want to put the money in the bank to fund my early retirement. I know that they love to see how responsible I am for my age, and my father completely understands, but my mother is like many adoring mothers - she loves to give gifts because it makes her feel good. My father told me, point blank «I understand what you mean, because I'm the same way, but it makes your mother so happy to give you a gift, she spends so much time picking out christmas gifts, imagining your face when you see it. Please indulge her once in a while, it won't hurt.»
I realize how fortunate both my sister and I are to have our parents. How wise they have been to both raise us in a way that we don't NEED money to survive, while also being able to help us to make our lives easier if they want. That being said, while my parents' division of the 20,000$ inherited when my grand-father died funded my first 10,000$ for retirement, the fact that I have never accepted any other money from them since graduating undergrad has caused my father to tell his friends and my mother how proud he is of me. Hearing my mother tell me that my dad was proud of who I was is more valuable than any money they could bestow upon me.