Here is an Update, sorry about the double post. I am up to 8.58gb of word docs already, it will be interesting to see how many word documents is equivilent to 37.2GB. Please post any comments so I know you are interested in this.
I guess he wants an archihve of like all of his old stuff and notes. I think it is really creative and cool. Hope you get it. also for the math if you don't want an archive just do that but at the same time it is just an estimate because of sometimes he could write longer or shorter so the size will differ and also you might not wanna fill the HD all of the way to or it will slow down.