This topic fits me recently. since I just sold a pin, and it was actually hard for me!
I've only sold 2 pins. Keep in mind that I basically have no cash to work with right now. I love the hobby though! SO...I juggle selling stuff to try to support the pin disease! It's kind of like a crack addiction to me. I'm just the bottom of the barrel guy at the moment and have to grab what I can when I can sometimes paying a little strong to get it. Everything is a project! I jump around working on what I can when I get the parts or materials to do it.
OK...On the one I just sold, I had to be a take it or leave it guy. Because of what I had in it. And being so broke at the moment? I can't lose right now. I felt so guilty! I felt the pin was in horrible shape. I did sell it to a fellow pinsider. So I was honest as could be. Took pics of any damage. Didn't hide a thing. To the point of him telling me "It's ok!!! It's what I'm looking for" since I was still pointing out the bad when he came to pick it up.
No, I don't look at it as a sucker/buyer. I actually hope the people are happy or know exactly what they are getting when they buy something from me. The price is always what I feel I need to have or what I'm willing to let it go at. I don't care what the "market" says. I've only sold 2 pins, but have been buying and selling in other hobbies, it's the same. I want a good reputation as being honest no matter what the price I have on it is. I buy the same way. Most people won't pay what I pay for some projects. I buy strong to get things that are closer to my price range. I offer high within my range.