I had a post all ready on my phone and LOST IT! Argh!
Let me see if I can remember all of it now that I'm back home at my desktop...
I tend to take "what ifs" like this and over think them, because everything is fraught with complications, fallout, and liabilities.
Example: You know, RedStang, I actually have sent a few $1 and even $5 bills off on balloons before, just a couple times, and I had thought of putting a yahoo email on it asking them to check in, but I decided not to - good thing too, because I also got lectured by a friend after telling him what I did. He has stories about balloons possibly being able to take down small aircraft and choke birds, etc... he's like that Saturday Night Live skit where the person always comes up with the fun killing side of every topic at a party to dampen the mood?
Basically, I would try to find a way to bring some joy into others lives WITHOUT it getting too crazy, or let's say, without it "corrupting" them in the process, so that would mean staying anonymous. If it was the Christmas holiday season, it would be easy to leave nice "Care" packages on the doorsteps of very poor families. I mean REAL poor ones. like third world poor in both the urban nightmare zones and the rural hovels all over the country. But then I'd fret about whether they would enjoy it for what it is and take inspiration from it, or auction off the goodies for cash ( like gift cards for groceries and stuff) to then get some nonsense and not use it on key things like their kids' school clothes or next months rent. I guess when you give you can only control but so far how its used, especially if you want to stay anonymous. I guess I would feel strange or even alarmed if I found a package outside my door. Some could feel that anger that comes from pride in thinking some neighbors are pitying them.
There have been news stories about a church or other charity that bought a homeless family a house, and one family took it and flipped it for the cash - still finds a more modest place to live but pockets the difference to the tune of like a 50K !
I actually thought if I hit it big - about getting a bunch of greeting cards with sappy positive phrases, and like a couple hundred bucks in it and hand them out to strangers that looked like they were carrying a dark cloud over them. I'd have to give onbe out and split to avoid getting mobbed. One Tv station had a Santa trying the hand out $5 bills and half the folks wouldnt take it because it was too strange.
Also thought about doing a money drop - make it rain one dollar bills over a safe area, like a plaza or park so no one will be running out in the street and get hit, or cars screeching to stop and have pile ups. I'd drop $1 bills so it can be a lot of them at a time, and so I could do it a number of times all over the country or world and not go broke! But then, of course I think of the possibilies of chaos, especially if it becomes a press story and folks try to anticipate where the next drop will be. There might be countless imitators that will do drops over unsafe areas and/or take credit as the philanthropist and try to get famous, like in that Dustin Hoffman/Andy Garcia movie(?) Smaller built folks, kids and babies could risk being trampled in the scrambles, or worse case, somebody gets fistfull of the dough and gets stomped by the nearest thug. You can't do anything without logistical headaches....
The crazyest personal thing, is I'd have to get, probably rent because I know I would eventually kill myself on it if I owned it - one of those "cigarette boats" like on Miami Vice ( look how old I am!) and run it up and down a few times. Its gotta be safer than wilding out on a high speed motorcycle or a drag racing run. I'd get my macho red blooded male testosterone thrill from it, and be done with it. I'm too old and out of shape to do anything crazy on a sexual/Charlie Sheen with his Goddesses level. I've always been deathly afraid of drugs and my rational mind would make me paranoid about STDs - dang it - can't even have a decent fantasy anymore - middle age is no fun!