I'm with Shevia. If I buy something pristine, I'm terrified to use it or wear it. If I buy something that is gently used, I'm fearless about wearing it or carrying it everywhere.
As far as the bag goes, for my part, I would request more pictures of that scratch, from different angles, and ask. If it's just a scratch, you can probably work with it. But the bottom part, towards the center of the bag, looks like it might be a crack, in which case I'd say, either walk away, or negotiate them down to a price that makes that scratch something you can live with.
If it's only a surface scratch, for me, it would depend on the price, and whether I thought I could make it work.