Pruchased some 1.25 x 1.25 aluminum angle to support the Rudder trailing edge while drilling. Set up the cleco'd rudder un blocks so that the trailing edge was level and then drilled every other hole. Used my shopvac to catch as many chips as possible during the drilling process.
When I finished drilling the trailing edge I discovered that the bottom skin (the LH skin) had shifted relative to the top skin such that the holes were nearly a full drill diameter off at the bottom edge. I ordered a new skin from Van's Aircraft and spent the week puzzeling on how this happened. I didn't come to a firm conclusion.