I don't watch IE Craigslist anymore, but I can tell you that over here, too many people price their tools based upon the prices they see (unsold) on Craigslist or some crazy idea that any tool with a little rust and a metal label must be more valuable than its new equivalent at HomeDepot. Be patient, reasonable prices and a few deals still pop up. Your advantage is that you are living in the middle of a huge market. I agree with the others on the value of that drill press.
The last two drill presses I bought were a 1950's Craftsman floor standing and a Walker Turner benchtop with a custom metal stand. The Craftsman had the variable speed adapter (broken but repairable). I paid $50 and $40 respectively and only had to drive about 3 miles to pick them up. That was maybe three years ago. I see deals pop up from time to time. If you are still in the market for one for yourself, just be patient. You'll find it when you least expect it. The next couple months are some of the best around here. People are cleaning out their garages in preparation for summer.