I have a commute that's about 30 minutes each way and 1 hour lunch
every day. That's two hours I want to fill by reading printouts of
interesting text and listening to interesting audio on my iPod.

For me PG essays would be the ultimate example of texts I want to read
and Venture Voice (podcast) would be the ultimate example of what I
want to listen to (others would obviously have different taste). I've
gone through that stuff repeatedly and tons of other similar content,
making it difficult to find enough new stuff to keep me entertained.

A site that let me assemble text-printout "playlists" and iPod
playlists for a week or more in advance would be great. It requires
measuring or guessing how long a given text (or book) is to see how
long it would last and organizing the audio into chunks that are
optimal for my given time allotments.

It seems kind of a weird maybe or niche, but it arose from a real
problem I have and I think it could be pretty big. There has to be
more people like me that want really targeted text and audio content
to consume on their commute.