based on my daysailer setup...
the rubber washer is first, then the metal washer (which when tightened down will compress the rubber washer... makes sense!), then the bolt, then goop it all with silicone, but especially under and around the bolthead and nut. Apply the silicone with latex gloves and smear it on, rubbing the silicone into all nooks and cranies, then with a light fingered clean glove take off the excess. When dry, it should FEEL slightly tacky as if there is silicone on it, but should look like there are no gobs of silicone.