Here's something simple: why doesn't iTunes link to the web? While writing yesterday's post I really wanted to find the webpage from which I downloaded the Malcolm Gladwell talk that inspired the idea so that I could link to it. In order to do so, I had to go to the IT Conversations home page, do a search, click a couple of times, and decide which of two Gladwell talks were the right one.
It should be as easy to get from a track in iTunes to a webpage related to that track as it is to get an mp3 on the web into iTunes in the first place: it should only take one click. It would also be really easy to accomplish. If there was a "URL" item in the id3 tags, iTunes could then use it to provide links to the web. Bands and podcast-makers could fill these in with their homepages or pages specific to each track. If empty, the links could be auto-populated with the page from which the download originated by iTunes itself.
With podcast subscription capability soon to come it seems inevetiable that iTunes will become more and more connected to the web. The process began when it became a user agent in the first place in order to implement the Music Store. And this seems like a pretty obvious next step.
Note: It's not nearly as good as Apple doing it, but this would probably be pretty easy to implement hackishly right now via an iTunes plugin that searched the song's comment field for a valid url and then added an "open link in browser" item to its contextual menu.