I can't comment on your specific question about which washers to try first but if you don't get a seal with the copper or plastic washers I suggest that you cut a washer from a piece of nitrile gasket material using the 7/16 steel washer as a pattern and put it on the bolt between a 7/16 steel washer and the filter top. Make the ID such that it's a snug, tight fit on the bolt. Moderate torque enough to stop the seepage and it should stop the leak. BTW, I purchased some stock hardware store 1/2 in and 7/16 steel flat washers last week and found the fitment to be the same as you described. In fact, the 7/16 washer was a snug fit on the 1/2 inch std thread bolt but would not fit on a 7/16 SAE fine thread bolt. If you need a hole punch try a large rifle spent casing on a block of soft wood. JMHO Stan