@Jim K., first off thanks for starting this thread. It was so good I put off my 2 hour walk that is part of my daily exercise routine. I appreciate your insights, especially into kids who are a waste of skin. I have helped form trusts for pretty rich folks, prosecuted lots of kids from wealthy backgrounds and from poor backgrounds. I have even been a trustee for a fair number of trusts. Extreme wealth in my experience rarely creates extremely competent kids, but it can. One of the most pervasive problems I have seen in kids from wealthy families is drug and alcohol addiction. For some they are just arrogant even when they turn up poor in later years. I have also seen a lot of poor folks with addictions and just plain obnoxious as well. Some kids were the opposite of their folks, some were identical to their folks.
I appreciate the mention by @Steve Vaughan about getting my insight, but when my kids were young I was frankly too busy and too ignorant to pass much wisdom on. I barely had enough for myself. I am pleased with how my children turned out, despite many sleepless nights of wondering if I was doing things right. I suppose the quality of my children is a mix of picking a woman who was a great mom and luck. Here are a few things that I think I did right.
I grew up nearly desperately poor. I finished my last year of high school on my own living in my car sometimes. I made my own money bought my own car and groceries. My kids earned what they spent. They had an old car to drive. If they wanted a nicer one they worked and earned it. They made payments with no help from me.
They learned by watching. Saying the right thing is not nearly as important as them watching the right thing. My kids never saw me do any illegal substance, or have more than 2 drinks in the same week. I understood that everyone can make mistakes. There was usually a lecture, if you made the same mistake twice it got ugly because you didn't learn your lesson so the penalty got ramped up.
I had standards and enforced them. If you wanted to go hunting with dad you had to be able to gather materials, and start a fire with one match. You could not do it, you could not go. You had to be self sufficient. My son once got stranded in the mountains and then an unexpected snowstorm hit. He built a shelter, had a fire, plenty of food, extra clothing, etc. When the storm broke and search and rescue found him he was leading his companion out in perfect shape, warm, and dry, on the trail home in a fairly bad storm.
I always told them the truth. Both children often called me mean. Telling my daughter that just lost a beauty contest that she had done very well in, that being a model or beauty queen was vain and more a freak chance of genetics rather than something to be proud of got me no love, but she ended up being valedictorian, and getting nearly a full ride scholarship. Telling my son who wanted to be a professional football player that he would never be a pro football player didn't go over well either. He was a wildland firefighter with the BLM and worked up to being the boss or assistant boss on fires with hundreds of firefighters and engines deployed. After having his own son he finally transferred into parks and recreation so he could be home and see his son grow up.
I really struggled to get a college degree because of cost. Several years saw me only going to college for 4 months and working the other 8 months to save up money. I told both of my kids that they would get a 4 year degree. It would be in anything they desired, and I would pay for it, but they would finish. My son was required to pay his own truck payments and buy his own food. He worked summers as a firefighter to pay for those. When he wanted to quit I went and spent a few days with him in his dorm room explaining why it was the wrong decision.
There were a lot of fights, I am still not sure if that was smart or not. Right was right, wrong was wrong. MY son burnt the clutch out of the truck one night out with friends. He paid the $800 to have it replaced out of his lawn mowing money. At $30 per yard it took awhile to pay for. They had their own bank account even in high school from money they earned, and they balanced it every month. We gave each child $10K for a down payment on a house.
My son hated the rental houses, while my daughter helped me work on them. We never had a new vehicle until I was almost 60 years old, and I nearly had to have counseling to buy that, even though it was in my business and a 100% tax write off.
I try to say things to them and encourage them to be smart about life and money. I feel I fell short in some areas, and great in others. I am proud of how they are raising my grandchildren. Now I have enough wisdom to pass it on, and plan to spend it fully on my grandchildren. My gifts are piggy banks, and money that they earn from me gets put in a Roth IRA for them.
I will leave most of my wealth to my children, but not all. My goal is to train my grandchildren and create generational wealth. In the end I can only give them the chance to be amazing, I cannot force it, but I can give them a greater range of choices than I had. I cannot put them into the dire financial condition I started in, but I can teach them my values. After that it's up to them.
Thank you everyone who posted I really enjoyed this thread.