My parents helped my siblings and I get started well in life. They paid for our undergrad degrees, gave us each a starter used car, and helped with house down payments, wedding gifting, and some grad school help. They also did contribute some to college savings for their grandkids. They also taught us a lot about personal finance and investing and education and work, which was probably more valuable than the helping dollars.
They also had enough to do everything they wanted in retirement and enough to take care of their medical bills with some left over, which we will inherit at some point, in our late 50s / early 60s, at a point where each of us have already made our own way. I'm retired and my sisters can retire whenever they get tired of working.
We were all very grateful and appreciative and have all paid it forward so now the grandchildren, all in their 20s, have a decent start in life too. None of them have college debt, they all have cars and jobs and are on their way to buying their first homes.
I inherited 1/3 of my Mom's moderate life insurance proceeds when she passed away. I didn't even think about it or even know the amount until after she passed away. She passed shortly after I retired, although the two events were coincidental.
Like my parents, I've helped my three kids with the education piece and have paid for their college degrees and helped them get started with houses and will help with weddings if/when that happens.
I also have been giving annually with a warm hand for the past five years or so. I gift some cash on their birthdays and Christmas, then do an annual transfer of stock. The amount of the transfer is something I decide on after looking at my own financial situation, which includes a very cursory calculation to see where I may stand in relation to the estate tax limit in the future. I also look at my WR% - to the extent I'm underspending I'll give more away because obviously I don't need it.
In my annual gifting email I always explain the motivation behind the gifting, the tax implications, and reasons the gifting might stop (if they do something horrendously felonious or if I need the money myself). I do monitor for signs of EOC (economic outpatient care - term from Millionaire Next Door book) and wonder if that may become a concern; I'll deal with that if we get there.