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I'd work from the top down, the oil filler gasket +valve cover gaskets+crush washers for it are cheap. Personally, I wouldn't do pressure washing an engine, although with a diesel, there's less electrical stuff to go intermittent or bad. Unless you are planning on showing it, I'd just use an old toothbrush,rags, and some engine cleaner. Once I got rid of the source of my leaks (the above), I cleaned the engine that way and the rest of the crud burned off eventually.
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