I've bought a lot of guitars online and haven't been disappointed yet. I've even bought two Taylor acoustics at this point, which brings me to my first point. I always assume that the instrument is going to need a setup to get to where I want it, whether I do it myself or pay someone else to do it, like in the case of my acoustics, which I don't work on. So I don't really sweat any of that.
For most of my life I always bought guitars as player instruments, and me being me there is often some kind of damage or wear from the playing. So I bought a Les Paul Studio, and didn't want to pay a lot for it since I don't really like that model. I'm sure any guitarist will understand why I would buy a guitar that I don't really like to have access to that sound, but my girlfriend sure don't. So I didn't really care what it looked like cosmetically, and it's kind of a relief to not have to care about it with a dinged up guitar.
Then I screwed up and bought some really great, brand new and beautiful instruments. Now I'm terrified of what will happen to them. So I guess in the future I'll draw some distinction between a playing guitar and one that I actually care about keeping looking new. So, now I'm one of those *******s all of a sudden.
I know this is long winded, but I wanted to put forth the idea that some guitars you buy just to play and play hard, so why sweat a detail or two that doesn't show in the pictures? And if you really care how it looks like, then maybe new is the way to go.