Husband and I play this game too when we get tickets. We have it narrowed down to...
Paying off the mortgages for the parents, brother, and the student loans of sister in law. You don't want to help people too much... "free" gifts made with the best of intentions can go really wrong. Like giving $5 mil or something... they can do what they want. When it's gone, they may have nothing to show for it, and come asking for more. Depends on what sort of people they are, and money can change people. So we'd put the funds towards something that truly helps and hope they make the right decisions from there (like not taking out another loan after you've paid down the first!). Since gifts over $10,000 are taxed.. we'd give Christmas family bonuses of $9,999.
Some of our family will for sure get bent out of shape. Our solution to that is equal gifting straight across the board. No favorites.
We'd set up a fund for gifting to strangers, instead of an actual charity. Charity makes giving too easy.. you write a check, they do what they will with it. Some of them... only 5% of donations go to actual work! So we'd be picky, wanting to check a charity group out on what they do, where the money goes, ect. We don't want to just start throwing money around.
Then we'd buy a travel bus, donate all our furniture and what not, and travel the US on the road until we see the land we want. I've traveled a bit, but husband hasn't. He wants to see the rest of the country before he chooses where he'll settle. I think it would be fun!
The other bonus to the road trip living is that we can go to where natural disasters strike, and give direct aid to rebuilding the area. By pass the charity, get hands on while writing a check for supplies too, to those that aren't covered by insurance.
We'd scrap our cell phones and get burn phones, to call family and keep tabs on them, while avoiding cold calls asking for money. We also wouldn't have a physical house for strangers to come knocking on.
We'd split the money up into different purposes... one would be for generating more income to further fund aid, through investments. A savings account that isn't touched, in case we run out of money elsewhere. Gifting money, a living allowance, a fund for building our own place once we settle on where that will be.
LOL... if only. Would be hard to remain incognito unless we kept changing buses/RVs.