I am struggling with this issue right now as well! It's time to redo mine. I'm trying to figure out how many strings I put on things, whether I do that for everyone or just for the ones who are struggling, and whether to try to use the will to "even out" outcomes among them or just divide things equally. What's the fairest way to do this?
Right now, my gut instinct is to do a trust for my two struggling ones that doles out money at intervals, as Kathy describes above. I don't think I want to put anyone in the position of deciding whether their plans for the money are "worthy" or not. When they were all younger, I had everyone in a trust with my mom as executer, with money only to be used for educational expenses, setting up a business, or buying a home. Now, mom's older and not the best choice for executer, and the only one of the kids who really has the head for it would be my youngest. It doesn't seem fair to her to put her in the position of holding the purse strings for her older siblings and making those judgments. And they are all kind of aging out of the kinds of education I had in mind when I put my current will together. So I guess it would be just age-based or time-based. I like Kathy's 1/3 at a time approach above. I'm fairly sure they would blow the first third, but maybe there would be an opportunity for growth and learning if a few years pass before the next amount drops.
But do I do that for the ones who are doing well now, also? N is married with a young family, struggling to make it financially, and a lump sum could make a real difference for them. Maybe let them get a house in their expensive real estate market. But he's struggled in the past, too, so what if he falls off the wagon again sometime after the will is written?
And then there's my youngest, who is off to a great start in her career and literally just married into a family of multimillionaires. Do I cut her out, because chances are she's not going to need it like her sibling will? Or is that making the wrong kind of statement - punishing her for her success and good fortune? And who knows, she could end up divorced and disabled at some point - anything could happen. I can't predict the future.
The bottom line is my modest estate probably isn't going to be enough for anyone to count on for too much. My first priority now is protecting my partner's ability to stay on our property for her lifetime, probably with some kind of trust that passes my portion of it down to my kids after she is gone if she outlives me. I have a little life insurance and my retirement account that could be divided. But it's not going to provide anyone with guaranteed housing for life, that's for sure. Maybe a boost into a more positive direction, if they use it well. But if I thought that would happen, I'd be trying to figure out a way to make it happen now while I'm alive!