I would like to start off with this: I dislike iTunes to an extreme.
To be fair, I access most all of my media off of a network storage, and it has irked me to no end that Macintosh is most certainly geared toward using your local drive exclusively. I am rapidly beginning to believe that Macintosh in general is not very good regarding accessing networked storage of any sort. The second option is that the home network is slowing, which I believe to also be true, and that iTunes is far too bloated.
I try running Winamp via Parallels and it works like a charm. Quick and easy. I reached the point where I have decided to switch back to Winamp, until I realised that I had already reformatted my iPod into HFS+ and would have to reformat into FAT or FAT32 to use it with Winamp again. About that time iTunes decided to work one more, so I was placated. For the time being...
My main quarrel with iTunes is not the fact that it is slow to change information and begin playback and to transfer anything, I can accept that as the consequence of network storage, my main issue is that 3/4 of the time, when I click and drag to add a song to my iPod, it simply does nothing. It won't drag the song. Updates haven't fixed it, and it seems to be random. I can find no pattern.
As such, I decided to try out some different music players/organisers. Here are the results:
Songbird - I didn't play with this one long; it disqualified itself quickly. It locked up almost immediately and has all the old downsides of iTunes and then some. The internet features are just adding more bloatedness to it. It took a slightly shorter amount of time to add music from the storage, but still, its playback was severely lacking, choppy, and just terrible.
YamiPod - This is a handy little utility for on-the-go listening to your iPod, but not really practical for much. It is a standalone application that you could just load on your iPod, but it lacks the ability to add music to your iPod (as far as I explored). It is handy as far as changing metadata on songs on another computer.
All in all, I miss Winamp.