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I've wondered the same. I previously planned (if i won the big lottery) to set up a $1 million trust with the idea that my work department could take 4% per year to purchase equipment. I returned to work at the end of the summer this week to find that the idiots who are now in charge threw away over $10k worth of stuff that i (and a bunch of school kids) need. Those fuckers aren't getting shit now and i hope i win just so i can buy my whole team into retirement and leave the fuckers totally fucked!
Back to the topic - i wonder about setting up some type of grant program. Maybe, as you mentioned, paying things for them instead of giving cash? Do you pay tax when you get a home through habitat for humanity? Can i pay for someone else's health insurance or fill their hsa account? Maybe a scholarship for their kids? Most people i know would be pretty happy to have $18k each year dropped into their retirement accounts.
Did a little research. You want to be in one of the 9 states that doesn't tax in lottery winnings. Fed will take 24% immediately and you'll pay the remaining 13% when you file taxes. The $18k gift tax limit is to and from per person. If the giver and recipient are both married, each giver can give each recipient $18k, so $72k per year from one married couple to another. Still trying to figure out the trust situation.