Yeah, I would definitely look into a used watch if you're finding you can't find what you want in your price point. Rolexes tends to hold their value relatively well, Omega a little less so...but you can still save quite a bit on both if you look around. You could definitely get a deal on a Baume & Mercier as that brand doesn't really have a ton of cache yet in comparison.
Personally, I find
http://www.watchrecon.com to be a good aggregator for used watches.