Brooklyn - I am not 100% sure there is no interaction with the whisky barrel and the tobacco. Commercially, the leaf is removed, aired out, and repacked some number of times over about a year. The barrier I saw in the C&D video might have only been put in for the last pressing or shipping for all I know. But other home processers I've read reports from seem to get a satisfactory product from coffee cans, lexan jars, or PVC pipe. Only time (or a message from Mr. Ryan or Mr. Oulette or their employees) will tell.
As to your second question, the first time, it was just "in order". Able to be handled and stemmed without crumbling. The second pressing, I misted and mixed a couple of times untill the leaf felt wetter, but it clearly still wasn't enough. I am thinking of steaming these pucks for a minute or two over boiling water to get them to a state where I can tease them apart, and then putting them back in close to dripping wet.