I struggle with the issue of having a mix of local and network music. The problem with sharing is that you can't copy the music to an iPod and you can't rate it. They have to be in your local library for those functions. I make extensive use of ratings and smart playlists to fill my iPod so this is critical to me.

I don't have a great solution. I end up constantly toggling the copy to local checkbox in the prefs depending on where I want the music to reside.

My biggest complaint about iTunes is that it can't monitor a directory tree for new files and automatically add them. Like everything Apple, it's all or nothing. If you use their workflow then things work brilliantly. If you don't then you are probably going to be repeating a bunch of annoying steps to accomplish a routine process. Oh yeah, I also find it really annoying that it can't recognize you're adding a duplicate song with identical tags that happens to reside in a different location.

The only really good album art proggy I've found is Windows only. It correctly filled in about 80% of my library with no user intervention. All the Mac based ones I've found are either one album at a time or choose bad search strings or choke on non-english characters.

I switched to the Mac about 6 months ago for my primary personal machine. I love the hardware. I like the OS. I tolerate the iLife suite. (But don't get me started on iPhoto. Oh how I miss Picasa and ACDSee.)


Edit: Check out XvsXP.com for a detailed overview of the differences in the OS'es. I find the number ratings silly because they are so dependent on your personal needs, but the content is excellent.