I'm totally digging iTunes so far. It's no end-all solution, but still nice. It does a good job of doing many tasks well and intuitively, but I'm still not ready to abandon winamp yet to play the quick and easy MP3. You can pry Tag&Rename from my cold, dead hands.
+I think it rips better than dBpowerAMP (for MP3 format, at least), uses a better CDDB.
+I have an ipod, itunes works better than ephpod (musicmatch is a virus, if you ask me)
+my 3500+ and growing MP3 collection is ripped, organized, and tagged properly and logically--it's slightly faster, but definately easier, to browse in itunes
+guess it's worth mentioning that adding my collection to the itunes library was painless.
+playlists are easier to manage and create, as is burning CDs (though I haven't burned a music CD since getting an ipod, but had an MP3 CD player before, and I think it'd be quite easier to make MP3 CD's with itunes from what I've seen).
+nice visual equalizer (stereo!)
-can't display the equalizer AND now-playing song at the same time
-minimized bar lacks in functionality (HOW do you get it to display the playlist?)
-music management was a little too intrusive for my taste, took a little getting used to and some tweaking.
-I don't like how it wants to add EVERYTHING it plays to its library.
-I think winamp has better keyboard shortcuts
-visuals are mediocre, and suck up a lotta resourses. (0-3% when playing an MP3, 85% w/ visuals, XP2400+ cpu)
-no multi-monitor support for visuals