CGrindahl
Online
Dedicated FM
Upload & Sell: On
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If you keep your eye on the board and have done a bit of research so you know what a lens is worth, you will occasionally find a great deal. I've scored big a couple of times. I've also picked up a fine L lens on craigslist for a killer price. Obviously, I knew the market much better than the seller did.
On FM you can tell when a seller has offered a great deal because buyers will be circling the ad like sharks when blood is in the water, pushing and shoving if necessary to grab the deal.
In my experience, decent deals often come from sellers who've been around a long time and who aren't insisting on squeezing every last centavo out of a deal. But again, as a seller you need to do your homework so you can move quickly when what you want is available at a fair price. Asking for photos from a seller with a great reputation is typically a sure way to lose a deal. Trying to squeeze the seller to make a better deal can also lose a deal. If you know the price and it is in the ball park, and if the seller has a good reputation, my advice is to grab the item. If you don't, someone else surely will... the early bird gets the worm.
I was talking with a friend about this last evening, recalling the old saw that a "sailboat is a hole in the water into which one pours money." Photography isn't quite as bad for the simple reason well cared for equipment can retain value. I've even made a slight profit on a used Canon 1D I bought on Rob Galbraith low these many years ago. It hasn't happened again, and I doubt it will with camera bodies. But lenses are like gold... 
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