While iTunes for Windows allows you to connect multiple iPod devices simultaneously to the same computer for charging, you cannot sync your data from the computer to all the iPod devices at the same time.
From http://rss.support.apple.com/ipod
You can easily connect guitars, microphones, keyboards, digital music players, home stereos, and speakers to your Mac. Learn how to connect third-party audio and music devices to your Mac, and how to configure them for use.
From http://rss.support.apple.com/desktopcomputers
