First I have to say I like iTunes. I don't buy any music through it from Apple but I do like the free podcasts. I also like the music player, specifically the ease of building custom play lists. However...
iTunes lost all my settings...again! Yes again. And I've had this happen on multiple machines. I notice it when I've left my computer on over night, with iTunes minimized and a Windows Update reboots my computer. As soon as I fire things up in the morning...poof! Nothing! I'm sorry that sucks.
Sure we could blame Microsoft for rebooting, but I set it up that way. I want critical security updates to fix and reboot my system. I blame iTunes for not properly saving my settings. Even if I lost the changes from the last time I opened iTunes that would be acceptable, but it resets it as if I'd never used iTunes on this computer before. Bad bad Apple.
I'm afraid it's time to reevaluate the alternatives. I've downloaded and installed Microsoft Media Player 11. I'm not a huge fan but if it doesn't loose my settings that's a plus. I'm also looking for Podcast aggregators. I'm trying Democracy for my video podcasts but I'm not sure if it does audio too. I like listening to a few audio-only 'casts.