Comment Let him exploit a Webgame (Score 1) 1095
I suggest to let him exploit one of those stupid and inhumane webgames that are out there in dozens. There is much fun in doing it and he will learn really a bunch of useful things about his system and programming also.
For example:
Take a look at a game like space4k.(com|de)
Show him a bit of java programming, show him how to use a library to web-datamining/testing like httpunit and how to do some simple things with that. Also do some funny stuff with java and sql based on mysql or the like.
Then go and try to build a working bot on that sort of game. Grinding-games like this one do not deserve that humans spoil their time on stupid clicking. But there is a great use for this sort of game: learning. And he will also will find out, that being smart is not always without problems, cause people really *hate* scripters in those kind of games.
He will have fun, he will have a live response to what he is doing (very life, I promise!) and he will have all up and downs that come with such a job.
By the way: programming in java and mining data, responding to web-forms is a really great sort of knowledge for the near and far future. Data is something like gold in our information society and to mine it with a bot is something like mining '49. It's just a game so nothing can happen, nobody is hurt (who counts).
java, sql, httpunit
Basetechnology with fun. And I promise if he even manages the captacha in the game he will be a smartass in programming and will lick blood.
with best regards -
most hated "player" of space4k.de
-by the way- i just see a captcha down here in slashdot. It would be fun to crack that one, too...