When I was in college, I came across a gambling strategy for online roulette. I tested it for a few weeks but I gave up on it as it was extremely boring and tedious, even though it seems legitimately profitable. A few years later I heard about bots that automate poker and so on, so I looked at tools that I could use to code up the roulette strategy to play it automatically. I looked into AutoIt and wrote some scripts, but the code ended up being beyond my ability to write, as my knowledge of AutoIt starting out was zero. Even a relatively simple game like roulette (only 37 supposedly random possible outcomes on a European roulette table) ended up having bot logic that was quite complex.
However a few weeks ago I came across this excellent article:
http://active.tutsplus.com/tutorials/workflow/how-to-build-a...
So I looked at re-writing the bot in Python instead. Turns out that writing it in Python is FAR simpler than AutoIt, and the code far simpler to figure out. Even though I had close to zero knowledge of Python starting out (learning Python really quickly by using it to build a real project, rather than learning Python theory first.) Now my bot is about 90% complete, just a couple of steps away from having a working (potentially profitable) bot.
Really cool what you can do in a few weeks in Python from a standing start.