I started working on a small script to generate "rain" bets using Electrum's "Create Transaction from CSV Text" feature. It's a working prototype, the code isn't great, but it's a solid concept to start with.
You can find the CSV Generator here:
http://jsfiddle.net/jadra/brt5kjdL/6/embedded/result/(JSFiddle.net is a free CSS/HTML/JS code sharing tool - this entire tool is just a web page and doesn't interact with anything except your browser)
It works with Electrum wallets right now, you can click "Create Transaction", then "From CSV Text" and paste the CSV it generates into the box to generate a bet of your choice.
The code is also available on jsfiddle here:
http://jsfiddle.net/jadra/brt5kjdL/6/Happy 1-year Luckyb.it! You're a great site with a great community and one of the best social gaming platforms I've seen.
Oh, this is sweeter than a sugar cookie with icing dunked in syrup.

Tipped ya 0.005 for this and I will be using it.
Wishlist:
* Toggle for the satoshi-organizer addition. Personally I don't care if my bets get mixed up and I'd rather not burn a satoshi or ten.
* Items in the list box should toggle rather than standard list box behavior (hold CTRL).
* Put the stuff that appears below the button in a second column.
* Sanity checking: Limit 150 bets, and minimum 0.001 bet. Maximum bets would be a nightmare with the randomizer.
* Reset form button.