About a week before iTunes was released for free, I paid 30 bucks for Xplay. I haven't loked back, but it'snot like I haven't thought about it...
One of the things Xplay adds is WMP support for the iPod. I can use WMP to send files over if I wanna, or use Xplay to sync with WMP's library. Personally, I skip both and just sync with a folder that I know I've gone through and corrected all the tags.
Another thing that Xplay adds is a whole mini-shell for your iPod. The pod may have to rename all your mp3s when they get sent over, and it may have to mix them into an inpenetrable file system, but Xplay let's you browse them in an explorer setting. Here you can add and remove files with real time drag and dropping. You can even Ctrl-select a bunch of files and drag them to Xplay's playlist directory, where it will prompt you for a playlist name, and then you've got a new playlist; the files get correctly filtered into the iPod's system.
I've actually never used iTunes, but Xplay gives me more add-remove options than I even need, and I don't have to boot up a seperate program and interface to browse what's on my Pod.
There has probably been some revisions since I last looked at Xplay, and the program was not without it's niggles: primarily the sync box that comes up with a 15 sec countdown,
"WARNING! Xplay is about to sync your iPod! Go hide under your bed!"
Couldn't it just do it in the background?
The more I think about it though, the more I like Xplay, it ain't free, but it's good.
Also, I just made a shortcut to Xplay's directory and threw that into my Send To folder. Now I can right click on an album or some files and do a "Send To" and they go right in.
Took me year to try this, kids