holy torque batman, that crush washer looks like it was put on by the hulk. Wouldn't surprise me one bit the dealer did that with a power drill instead of by hand with a wrench. I've never seen one that buggered up and deformed. Dealer recommends oil crush washer replaced everytime probably because, and I have experienced it with toyota dealers 1st hand, their oilchange flunkies crank the drain plug on with a power tool or use their muscles way too much cranking it on too tight. My former toyota I had dealer do first oil change for free ONLY the first time. The 2nd time I did it myself and the oil drain plug crush washer was permanently embedded into the oil pan when I unscrewed the drain plug it stuck on and wouldn't come off. I had to take a fine metal screwdriver and chip it off very hard to do - fricking idiots. Personally, I let my crush washer go every 2-4 oil changes since I don't use monster cranking power on the drain plug and it will last just fine, but for sure replace every 3-5 oil changes just to be safe. My .02 cents.