My parents have been super helpful and generous. They paid for me to be privately educated from 11, and supported me through university - paying all my living and accommodation costs. They paid for driving lessons and bought me my first car.
They are not overly rich and live quite frugally (by choice), but saved carefully and inherited money too. An elderly neighbour with no family left everything to my mum, so when I was 5 my parents moved and were able to buy a family home outright. With no mortgage, this meant my parents could afford to send me to private school at 11. My dad was an only child and inherited the estate of his parents and an elderly unmarried aunt. Neither were huge amounts, but he was the sole beneficiary of both estates, so in total this was quite a sizeable amount. I was close to my grandparents and Great Aunt, and they both wrote in their respective wills that my dad was to use the money to help me financially with anything I needed (as I am an only child too), so my dad often uses that money to help me with sensible things - such as paying for our new boiler, car servicing, school holiday clubs for DS, etc. He also used the money to give me my deposit for my first house, enabling my now DH and I to get on the property ladder.
We have one DS7 (their only grandchild) and my parents now have savings accounts and a pension fund for him, so he will be financially secure when older. DH and I both work full time and save for our son too. He attends a good private school and does not want for anything. We are by no means rich in comparison to most of his school friends, but it's comforting to know that we have the financial support of my parents should we need it. I feel incredibly lucky and thankful to them for allowing me to be in such a privileged position.
My parents are very open about their will and future wishes, and I will be the sole beneficiary of their estate in time. They have lots of special trust funds set up and this will enable DH and I to live very comfortably and to put money aside for our son's schooling, University, first car and house deposit. I want him to have what I had, because I know how lucky I am and how much it has helped me to get on in life.
DH has a very different background. He comes from very little money, yet is good at saving and making sensible financial decisions, because he knows the value of money. We hope to pass this on to our DS, as I am guilty of sometimes spending excessively or frittering away money on silly things...