I can't believe the comparison with the Connect Store and Itunes. Itunes has functioned just about perfectly from Day 1. You never heard the complaints like you hear on this site about the Connect Store.
Also, when the Itunes store updates, it is usually to add features or functionality.
Let's remember that Sony still hasn't provided any Mac support...at all...since the Reader was launched.
Also, there has been an update for Itunes that addresses most Vista issues and allows you to sync your Ipod. Still a few issues, but it is workable. Here's the link:
http://docs.info.apple.com/article.html?artnum=305042