The oil pan drain on my 216 was a little on the rough side, so the drain plug with copper washer dripped a little. I replaced it with a new plug and nylon washer, and even after several oil changes, no drips. I think the nylon washer compresses into small imperfections on the oil pan better than copper. I would think the face seal o-ring would be good also.
Always had good luck with Felpro gaskets - but, I have never used other brands. I am curious to see replies on the head gaskets also.

1938 Chevy 1/2-Ton
In the Stovebolt Gallery
More pix on Photobucket