There is a danger in upgrading one's lifestyle excessively and losing oneself in the process.
I think that once there's enough money to stop worrying, then any further dollars have no value. Paradoxically I feel an onerous stewardship obligation of optimizing the use of those worthless dollars.Beyond that I think it'd be more of a burden.
You would think that if you had an extra $25K and wanted a pickup truck then you should sort through Craigslist, take a candidate to a mechanic, and buy it. Done. Next project? Sell it or throw it away when the floormats get dirty, because you bought it with dollars that had no real value to begin with.
But no-- we obsess over those worthless dollars to optimize their value at picking out exactly the best truck for that price. Or maybe chipping in a little more for a "better" truck. And then we optimize the quality & lifespan of that truck even though we could just go buy another one.
And maybe the worrying never stops because there's always the specter of "But what if I'm wrong and I really NEED that money someday?"
I'd pitchfork the green waste onto the next generation, but I fret about affluenza & entitlement. I've seen that among a few shipmates in my generation and I don't want to create another one. The problem is that I don't really know how to avoid creating one-- other than to give them enough money to suffer from its effects and learn to cope with it while hopefully not becoming addicted. Sorta like "teaching" your kids not to be alcoholics by making them drink enough to puke their way through a hangover. I don't want to get into how I chose that analogy.
I'd shovel the green waste into a 529 for the college fund of the third generation, but intellectually I know that growing up with "Grandpa's saving for you to go to MIT" is not exactly the same as having scholarship skin in the game.
So for now the best options seem to be annual charitable donations and, waaaaaay down the road, perhaps endowing a college scholarship program.
I enjoy surfing at White Plains Beach on the last Wednesday morning and the first Saturday of the month. Those are the days when AccesSurf sets up their equipment and their beach-mat track down to the shorebreak for disabled surfers. Some of them are kids with mental and/or physical issues and some of them are adults in wheelchairs. I'm amazed at the variety of floating objects that are put in the water, and I'm even more impressed by the people who are using the equipment and those who are helping them. I have no desire to join the volunteer crowd (it's hard, hot, sweaty work), but I enjoy watching it take place while thinking "Hey, I helped pay for that!"
We donate to a food bank and a homeless shelter, too, but watching their programs in action doesn't exactly deliver the same sort of psychic kick.