I'm very detail oriented when it comes to my purchases. I'd like to enforce pictures of the actual product - front, back, contents, open box, front/back of media (top/bottom if optical). I use auction sites for reference for the site more than I use for my own, but I stopped using auction sites because of how much I've been burned by the small amount of things I've purchased. 6 of my last 10 purchases I had to send back for refunds because they either sent the wrong item, or it wasn't in the condition I expected/wanted. I'll spend an extra 20% if I know exactly what I'm getting.
I wonder how hard it would be to have a mechanism that promotes picture taking as you described, or incentives to describe items more diligently. In the past I thought about having a series of simple Yes/No questions related to each system category that would determine a numeric grade. For example, if you wanted to list a NES game, there might be questions related directly to the condition of the cartridge's label. The challenge would be to come up with questions that aren't ambiguous and that are still useful, that could be answered quickly, and then weighing their importance in the product's grade.
I would prefer to avoid shipping all together and buy locally, I'd just like to have a site where I could see exactly what my local community had to offer rather than having to browse through an endless stream of disorganized or non-standardized classified ads. Thanks for the feedback. =)