Updating my Windows iPod

New stuff came out for the iPod. I am always confused by the software version. The windows updater 1.3 was highlighted on the Apple site so I downloaded that. Then I found out I have updater 2.0.1 on my system, which is newer. So the installation won't start. Seems like there are two different series of software. The 1.x series are for both styles of iPod, and the 2.x series are only for the iPod with dock. Trying to install the latest 2.1 software, and I found that I need to upgrade my Windows 2000 to SP4. Five or six reboots later, the software updater updated my iPod. I have yet to test to see if it fixes some of the problems. Meanwhile, I downloaded the new iTunes for windows and installed it ---

The new iTunes is great. However there are not enough documentation on how to use it. Anyone knows what is the blue checkbox for at the beginning of each song title? And, how do I sync the iPod if I do not have iTunes set to automatic sync?