If you dislike iTunes as much as I do, Anapod by RedChairSoftware is the perfect alternative.
I find it extremely easy to use and the interface is aesthetically pleasing. Anapod is integrated into Explorer.. You can right click a file or folder and “Send To” Anapod.
The SpeedSync is great. I hated how iTunes would delete all the crap off my iPod w/o confirmation (and this is a default setting?) With Anapod, it syncs then it shows two panes of whats on your PC thats not on your iPod and vice versa. It then gives you an option to transfer one or the other or both.
The software is $25 but I’d pay upwards of $100 if I had to. It makes life sooo easy. And making Contacts and Notes is as easy as Right-Clicking and selecting “Make New Contact”. Or, you can Sync with Microsoft Outlook. You can also copy Data files to your PC and back with extreme ease. Just drag and drop.
Additionally, it has a built-in Web Interface so you can access your iPod from across a LAN or the Internet. It also auto converts WMA files and other formats. For more features, check out their comparison page.
Oh, and big nerds can run SQL queries on their iPod music collection :D