As far as weather proofing the wood, the supports are oak wich is weather resistant and it got coated with some polyurathane. I have no clue how much it will hold, but it only needs to hold a trunk. Concidering that the kayak I recently build uses the same two species of wood, I actually do not expect it to fail for reasons of the wood. The cutting board is obviously weather resistant.
As far as the metal rack not fitting... My guesses are that the rack is higher because of the lack of eyelets and its a very racing inspired frame so the seat stays have a very steep angle which probably brings the rack closer to my seat???
Regardless, thanks for the comments. If anyone is curious to try and replicate it on their own bikes, I would be glad to offer advice. I seriously doubt this will happen, though. If anybody is riding around Durham and Duke and you see a real funky rack, you will know who owns it.
Thanks all
Scott