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Consider, it's up to you but consider, that you might get more joy out of gifts while you are alive to watch the recipients benefit from them than you do out of imagining how much they'll benefit from bequests you intend to leave when you die.

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That's how my grandpa lived: A life full of fleeting moments now in exchange for shellshock when 65 arrived.

Given the reluctance of our culture to show care and concern for people in general, I'm not too psyched about getting to the end and needing a handout.

Would you rather have a handout or a heavy heart full of regrets?

A valid concern. But estate planning lawyers like to remind people that it's quite possible you will get more love and attention from your relatives in your old age while they are still expecting an inheritance than when they know you have already given it to them. A bit cynical, but relevant to consider.

I sincerely hope that when I'm that old, I'll be above such pettiness.

Sure, if the only good thing you ever give them is money, this may true. But if you are actually good to people, not so much.

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