I just stumbled across iTunesWatcher 2.5 which is an applescript based app that posts active tracks from iTunes automatically to your site… There are definitely other apps or ways to do this (like Kung Tunes), but I think this one is the most sophisticated yet simple to configure. I’ve set up a page to track my listening… will probably work in more into the flow of my site when I get more of a chance.
My only glitch so far is that my music is based off of a different machine than the one I am on, and the applescript does not seem to like that too much for now. I copied the library file from the other computer to my laptop and am connected to the remote drive storing my tunes to stream and that works.