A story of what can happen to ya if you get rich real fast. (Though I guess no one has to worry about that for a while, since the system seems to have gone back to channeling more money to the rich, instead of giving out the odd million to programmers in a semi-random way.)

The Monty Hall Trap is a real mind-bender.

David Gelernter's latest project is Scopeware, which appears to be fairly similar to Lifestreams (which is apparently dead). Essentially, a time-based view of computer tasks, which makes a lot of sense in a certain respect. I don't see why some kind of rudimentary time-based view of work couldn't be built into traditional systems; e.g. in addition to having a list of directories, why not also have a parallel list of files, organized by date and time. I wrote an article about this back in high school, called Liquid File System. While that article needs an update, bad, I think it has a lot of relevant points. Here's an illustration of how I imagined alternate hierarchies of information being displayed back then:

Having auto-generated views of web directories based on data like dates or categories would be pretty useful, too. What I didn't know then is that there's a word for this: intertwingle. All that means is that things can be connected not only by category, but by size, date of creation, keyword, author, or any other information that one might have (stored in a computer). Jamie Zawinski explains intertwingularity fairly well in this proposal for organizing email.