I've not used Anapod, but I have used Notmad (Creative players) and Dudebox (Dell players). Both are great and much better than the Creative/Dell software that came with my players.
Not having an Ipod, though, it does seem like there are several free options for Ipod owners. The advanced features of the Red Chair software are nice, but it would be hard to justify paying for it if there is a freeware alternative that works almost just as well.