If you're not packing an iDevice and don't want to use Windows' default media player, you're still spoiled for choice for good media players and organizers. That said, WinAmp is an old favorite in the field, featuring a highly customizable interface, iTunes music importing, folder watching in order to automatically update your music library, podcast and internet radio support, as well as a very good plugin system. WinAmp also handles syncing with Android devices quite well. Additionally, if you've also installed the WinAmp Android app, you can even sync your device to your desktop library wirelessly.
Verdict:WinAmp is a solid media player and library management program, with a customizable and skinnable interface, as well as good plugin support for expanding functionality. Android syncing is also a snap.
Note: WinAmp's installer will try to add in extra programs and toolbars during installation, so keep an eye open.