It's nice to see somebody else from Windsor here.
I've recently spun off all my older gear that I wasn't using. I may have some older stuff I lent out coming back soon, maybe in the next few months. If/when that happens, I could probably help you out a bit...probably in the range of free. Hang out in the forum for a while, learn what you can and we'll see what my buddy returns to me when he upgrades.
Edit: It seems to me that with that budget, a good set of headphones will be the best option. I don't mean the Best Buy/Future Shop overpriced Bose/Monster brands, but rather something that's more quality oriented like a Grado or Sennheiser. The best part of that is that you could crank the volume without bothering your parents. Some people here will swear by their headphones for quality music reproduction.