...the more I appreciate iTunes. Seriously, you're missing out if you don't have it yet.
Even though it's been well over a year since I've switched over (so newer versions of Winamp might have had improvements), I can still confidently say iTunes is far superior.
There's a "library" with every song you've ever played or dragged into iTunes, so you can look through your collection in one place. It also remembers artists and albums, so as long as I know Tachibiana's seiyuu starts out with "Kawaha--" it fills in the rest for me. Here, the browse feature I never use (because search is more convenient).
Can create "smart playlists" using various specifications (they're purple. XD aha~). My Okiayu s-playlist - every time I add another song with him to the library, it's automatically added to the playlist.
Handy for those songs by a specific seiyuu scattered about different folders, but the drawback is that I can't manually delete tracks I don't want, i.e. the talk and karaoke tracks. I had to go in and remove them from my library (but not HD). I like s-playlist for BL dramas and radio shows though as I already label them as such under genre... and if I had consistent favorites, a fave list using ratings would also be convenient.
Control over which fields are shown for each playlist, and the width and order of those fields.
Can automatically reorganize each list by any of the shown fields. I have most of them by album, with the shuffle and repeat-playlist options on.
Multiple playlists on the left toolbar for fast-and-easy switches. And yes, you can hide the artwork so you have less scrolling for your playlists.
Search option, to quickly find a specific song (or songs by the same artist, series, etc). Here, I typed in "full" in my shoujo playlist, and all the ones without that exact phrase in any shown fields disappeared. I often use this to temporarily isolate Minagawa Junko songs on my PoT list because I don't want to bother with a separate playlist. =P
No character limit for each field.
Can change info for multiple files at once. Very helpful for uniformity and organization.
Can specify start and stop time for each song without altering the file in any way. What do you mean Days of Moment starts off with a loooong, slow Fuji-solo intro? It starts with Taka-san singing as far as I'm concerned. =P
Easily re-encode those pesky 320-kbps mp3s to smaller bitrates (while doing/listening to other things). By setting start and stop time for the song beforehand, you can copy only the parts you want. There's a join file option, too, but as I've yet had a need for it, haven't figured out how to use it.
Simplified importing and burning.
Summary of # of songs, total time and size for each playlist at the bottom. Although sometimes, I think it's better not to know. I get overwhelmed knowing I have
over 24 hours worth of BL dramas I have yet to listen to and put them off indefinitely. ;-; I can't even get to the midpoint of the Zoro x Kiyomaro Nakai Kazuya x Sakurai Takahiro slash, as yummy as the two sound.
A bunch of other cool little things I won't bother listing.
The only annoying thing was that by default, iTunes creates duplicates of each file to put in a separate folder (thus eating up HD space unnecessarily), but it's easily changed in preferences > advanced (uncheck "copy files to...") Oh right, and if your computer's a piece of junk from the last century, it probably won't work because it's too cool for you.
So go download it~! =D It's free (because they're hoping you use it to buy stuff from their online music store), and it's the coolest application EVAH.