Well DRM avoidance, was the big factor for me, but it will be for you too now, as for a start you should copy all the stuff off your ipod to a safe directory that has nothing to do with itunes, where you can treat it as a storage vault, so that if anything goes wrong, youve got something to go back to as a safe backup, it'll take a while if you've got a few gigs of stuff on there, but its worth it. The software just treats your ipod like an external hard drive, the clever bit is where it interfaces with apples ipod structure.
I've found there are protocols you need to follow, like having the manager started first in the systray before connecting, and asking the software first to disconnect, before unplugging, so that all changes can be saved.
I'd suggest if you go for it too, that you kick itunes into touch in that, it may not let you reload stuff from itunes, if you deleted with anapod for example, this is where the DRM crap fecks things up, so your better using wholly one system or the other. I cant remember the full story, but I think you lose some features such as the delete duplicates feature of itunes, and of course Anapod is not a player which itunes is, just a file organiser, but then you can sync another working directory (not your backup one)with the ipod using Anapod, and just use your normal media player on your pc to play the stuff from that directory and get shuffle functionality etc from your pc if thats where you want to play the stuff from. Where you are just using your ipod away from the pc, it functions perfectly normally as it always did on its own
But read all the FAQ's on the Anapod site first and be sure that its not too techy for you although it should'nt be, as most people have used explorer, since you might consider that whilst itunes can be awkward sometimes and doesnt give you the results you want, it is reasonably simple, although a buggeration when managing your files due to DRM etc