I just installed a modified version of this bulkhead fitting, (thanks Bobby M). I really liked the idea of the PVC ring to stabilize O-ring; but once I got the original Rubbermaid cooler valve out I realized how thin and non-parallel the spigot area is. I also didn't want to drill out the outer shell if I didn't have to.
My final fit-up put a second O-ring inside the cooler wall space, sandwiched between both the inner and outer ply's of the plastic. I used dash 315 O-rings that are a little thicker than the 314 rings. Because the O-rings are flexible I was able to persuade it into place with some gentle pushing and prying without over-sizing the outer hole.
I was also able to get away with only a single washer inside and out, possibly because of the extra thickness with the O-ring(s). But I did have to grind the OD profile of the outer washer to fit the outer spigot area. The molded orange plastic recess was interfering with it sitting flat.
I tested both boiling water and ice water for 24+ hours and have no leaks. Thanks for the input everyone!