As always, it depends on supply and demand. Right now with the construction business in the dumps, used skid steers can be had cheap and there is little market for them. Part of that also depends on where in the country. In places where the housing market has totally crashed, you probably can't give away a
ss.
Also, finding a new
SS for $20K means the small end of the range and the resale market for those will be more limited than a larger machine.