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hankronI sell (and buy) almost exclusively uncataloged/rare items, and I almost never predict what an item will sell for on eBay. One thing higher than expect, one lower. As I don't take consignments and don't have a problem keeping what doesn't sell, one can judge my opinion of an item based on it's minimum bid.
I don't think one has to be Scott Gaynor to sell stuff well on eBay. If one slowly gains a good reputation through buying and selling, one shouldn't have trouble selling. Be honest in description, buyers love quick and good shipping (most common comment in postive feedback), be polite and helpful to buyers. The key is not to make a single sale, but to get that buyer to come back again.
It is my strongest opinion that a seller should be painfully honest in describing the item, including being conservative in grade. Don't try and slip stuff by or hope the buyer doesn't notice. Pointing out unseen flaws may hurt on a particular sale, but it only helps you in the long run-- and is what gives a person a strong reputation in the hobby.
If, when writing your auction description, you include details that you really wish you didn't have to include, you're being honest. If you exclude the details so as to gain a higher price, you're being dishonest ... If the buyer opens up the package and thinks "Exactly as he described," you have a repeat customer.