That really depends on the pin.  Very true, you can get some steals if you find pins that are labeled poorly.  But, as a Stitch collector I have watched lots and lots of Stitch pins this year.  It all depends on the design of the pin.  This one for example, I want it, and someday when I have some extra cash I may go as high as $50, but right now, there are more important pins to get and I think that is where a lot of people are at right now.
There are surprisingly quite a few pins being released lately that are in high demand.  I for one have an addiction to the PODM pins so my Stitches have been taking a back seat.  A lot of older pins are down in value right now so it is a buyers' market.  I'm just, like many others I'm sure, just spread too thin on pins right now.