I was in the same position a couple of months ago, looking for my first pin and trying to find a relatively new (i.e. at least a solid-state) machine for as little as possible. I scoured my local CL for deals for a few weeks and came across a few decent finds - a Monte Carlo and a Space Shuttle for $800 each, and a High Speed and a Tee'd Off for $1,000 each. With the exception of maybe the MC, which I've never played, those are all pretty fun and relatively decently reviewed games in your price range.
Eventually, though, I decided it was worth spending a little more to get something slightly newer that I was more excited about. I found a Goldeneye on CL and the seller turned out to be a fellow Pinsider. I made a great contact in the community and as a result have met some more local pinball friends in the process. Anyway, my advice is to maybe try saving a little bit more to put toward your first game, play a bunch of them and make sure you get something that will hold your interest for a while. Above all, be patient - the right deal will come along eventually. Don't buy something just to buy something, or you may get bored quickly. But hey, even that should be a learning experience! Good luck!