My PEACE OF MIND rules for buying used: If I can't save at least $200 or more I will buy new because If there's something wrong with the lens there goes your savings and now you have a used lens that need repair for the same price of a new lens that has a warranty, plus $200 or more savings would cover Canon's minimum repair charge if the lens need repairing.
When buying used try to buy from someone who's bought/sold before. There is a "positive feedback" thread you can check out.
Ask for sample pictures. I bought a used Sigma lens once and got tiny sample pictures. Sure enough, it was a bit soft at f/2.8 at 200mm. I ended up reselling it to someone who used it for video purposes. As long as the sample pictures are nice and large and look good, the lens should be fine.
And finally make sure the lens is insured for shipping. If something isn't right with it, you can possibly file a claim against the postage company to have it fixed.



