I also end up doing really well buying used tooling on ebay. It is usually old but good stuff that has come out of closed up machine shops, manufacturing plants, etc. I try and pay about $1/tool in a lot of 20+ items. What I have found is there is always at least one tool included that is worth more individually than I paid for the whole lot.
Not a good approach if you are looking for something specific, but if you are looking to add to your general tooling collection it works well. As a hobbyist I'm able to get by pretty well picking things up on ebay and from my local metal scrapyard.
Unless you are paying for the really top notch production tooling, I think you get much better quality buying used.
As an example, I paid $25 including shipping for these -