Usually with oil on the outside, the boot gets worn enough to cause the spark to travel outside the plug somewhere other than the combustion chamber. Absolutely change the valve cover gasket, and check the oil filter adapter for leaks. It can blow back while driving and coat the back half of the engine, but usually it gets the starter. If the misfire isn't cleared up by changing the rail (I'd do just the boots, but that's me) then I'd swap the last 2 injectors to see if the misfire followed the injector. If not, do a compression test.
I think you'll have it nailed when you change the rail though.