I've become a fan of the Shed of the Week posts on Pistonheads. A shed is, apparently, a used car costing under 1000 british pounds for sale in the Pistonheads classifieds.
So... how about a TCL version using autotrader, craigslist, ebay, etc....? At this moment, 1000 pounds converts to $1614, so we could round up to $2000 if necessary.
Best or most interesting used car for under $2000. Let's see 'em.