Good news: back in October I wrote up my notes from Umberto Eco’s lecture on “How I Write”. That one and his other 3 Ellmann Lectures are now available on iTunesU.
Audio and video from the New York Public Library is now on iTunes.
This page has some awesome ideas on taming iTunes for classical music. I don’t think I need to go quite so granular with the tagging, but the article nails one issue right off the bat: the Gracenote CDDB is a HUGE thorn in the side when it comes to classical works.