Originally Posted by zacster

Start by shopping around the bike shops to see what is available and what they feel like. While you can get good deals on used bikes off ebay and CL, if you are not somewhat knowledgeable you won't really know what you're getting. The ebay listing above is a good example, I don't think that's a good deal at all. That looks like a mid 80s type of bike and you can get those cheaper. A good deal on that bike would be ~200. If you are buying used you want it to feel like you're ripping off the seller, while the seller is still thinking "good, I got rid of it and got some cash". Both sides are happy.