Paid $400 out of my own pocket at 15 for my MIM Strat. I came home and was playing it and, like a fool, I forgot I was wearing a watch. I scratced up the finish pretty nicely. Add in a few scratches and that, and I'm okay with it. I modded it out and made it a dream guitar--I love it.
My first bass was a '94 MIM Squier J that was my older brother's. It had already taken a few dents and dings, so it didn't bother me as much. The finish has cracks here and there, I think due to the heat and humidity of the summers and the cold and dryness of the winters that it experienced over the 10 years it sat in a basement closet.
About a month ago, my MIM Agave Blue P fell off the strap and smashed off the concrete floor, taking a nice piece of paint with it. I was (and still am) pretty heartbroken over that one, especially because the color has gotten extremely hard to find and is near-impossible to fix.
If it's a natural wear pattern, I'd be fine with it, but when dings just take out nice chunks of paint, I get a bit upset.