Question : iTunes Management

Set-up: iTunes on a Windows box thats main purpose is to feed the Apple TV,  MacBook Pro with iTunes, 2-iPhones, iPad, iPod.  Apple wireless network with one TimeMachine Airport Extreme plugged into fibre and two Airport Expresses to extend range.

As my Apple network has become more complicated-sophisticated, I find my control with iTunes falling seriously behind.  Is this a failing of mine where I just don't understand how to set-up and run a an iTunessystem, or is iTunes falling behind as an entertainment system management tool?  

With AirTunes and Home Sharing turned on, I've just got a muddle of podcasts, music, videos, and apps (not to mention files) ranging free all over my network in a confusing jumble depending what's plugged in; underutilized storage and no way to back up my purchased movies on Apple TV to a hard disc or to a back-up service.  

 iTunes is beginning to feel like it's just not up to the challenge, but perhaps it's me.  Are their guides or how-to videos of getting this mess under control and rationalizing it?

Answer : iTunes Management

It's not you, it's iTunes.  You are at the bleeding edge, with your multiple devices, etc., and iTunes is designed for the 99.99999% of people who just want to sync with their ipod.

You might want to consider experimenting with MediaMonkey ( http://www.mediamonkey.com ).  It's free, and is kind of an "iTunes for power users."  I'm not sure it'll do everything you want (and you'll still need iTunes for some tasks, like downloading podcasts from the iTunes store, which, last I looked, MediaMonkey couldn't do), but playlist/storage control is something that MediaMonkey is light years ahead of iTunes on.