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All the t-nuts are nicely pressed into the board.

I ended up using a 9/32" drill bit which gives a .281" hole, still a press fit for the .291 t-nuts but loose enough that I didn't think I would destroy the wood.

I ended up using a shop arbor press to push the t-nuts into the base of the board. I ended up having more control than using a hammer. Using a clamp is a great idea (basically the same principle) and I would have used that if I didn't have access to the shop at work.
http://images.google.com/images?q=arbor%20press&ie=UTF-8&oe=UTF-8&rls=org.mozilla:en-US:official&client=firefox-a&sa=N&tab=wi