Earlier tonight, Apple released iTunes 7.0, mainly a vehicle to allow the sale of movies through the iTunes store, and an update to the video iPods to allow them to play downloadable games. I'm happy because the updates fixed a few of the biggest problems that I had with the iPod/iTunes combo.
First off, they fixed a simple problem by having the iPod's screen stay lit (at the minimum brightness) when it's connected to your computer. This is useful because when you dock your iPod, the screen changes to a flashing "Do not disconnect" message that you can't always see if the screen goes dark. Since the iPod is charging anyway, there are no worries about your battery going dead because the screen is on.
Second, I had a weird problem that occurred most of the time when I docked my iPod. It would forget what I had listened to! If I listened to 10 podcasts before I docked, and then checked the status of my iPod in iTunes after I docked, my iPod would forget that I listened to those 10 songs. What a pain in the ass! More often than not, I found myself scrolling through those tracks again, just to mark them as played. I had heard from some of my Mac-using friends that they didn't have this problem, so I think it was probably only a PC thing.
Combined with the small little utility I had to write to monitor my podcast share on my server machine and automatically sync the new shows to my iTunes library and then to my iPod, I'm quite happy with everything now. My next step is to write a service to continually monitor iTunes to see if my iPod is docked, and then to do the syncing automatically instead of having to run the damn thing manually.