I've bought two lenses used online one from KEH and one from POTN classifieds. It depends where you purchase from, from KEH I didn't get any pictures of the lens, or any idea about if it was a sharp copy, but they are extremely conservative with their ratings so I trust their ratings. I got a fantastic deal, and the lens looked brand new. I would have been able to return it to them as well, had it not been what I was looking for.
When buying online from a personal seller, you're correct in wanting a picture of the rear and front elements, any blemishes on the body, and a few sample pictures so you can ensure there are no blatant defects/problems with the lens. Original box/warranty card aren't necessary in my opinion, but they are always appreciated.
In person, always try the lens out, make sure there is no mold growing inside of the lens, and that's about all I can think of.