I’ve been a Winamp diehard since the beginning. Back before CNN even knew what MP3 was, I was using my 14.4 modem to download, download, download, and using Winamp to listen, listen, listen. I love WinAmp and have been a loyal user since v1.0, but I have to admit that the past couple years have left much to be desired. The way we listen to digital music has changed over the past couple years, and Winamp was starting to feel inadequate to handle things like 35GB music libraries. On top of that, it just doesn’t seem stable or fast any more. Here are some problems I’ve had with WinAmp:

• The random shuffle sucks. It often seems to like a certain “section” of a huge playlist and stay in that general area. If I’ve got 20 days-worth of non-repeatable music in my library, I shouldn’t be hearing the same band 4 times in an hour.
• Winamp doesn’t seem to “watch” my library folders very well. In otherwords, if I rip or download some new tunes and stick them in my library, I have to manually re-scan my library and wait 5 minutes for my new MP3s to show up. Sure, I could just schedule a rescan to automatically happen every minute, but that’s rediculously slow and unneccesarily bogs down my system. I want my new music files available for play now.
• As much as I like the modern skin, it sure is a resource hog
• WinAmp doesn’t support the newest ID3 2.4 tags. They’re great for album artwork, grouping (eg: compilation releases, multi-disc sets), auto-normalization for quiet tracks, etc.

I fear change, but these problems more than encouraged me to try out Itunes to see if it would solve them. While it’s been cool so far, there are some things I miss and/or don’t like. Here are some comments:

• The Song Name column is stuck as the left-most column in all views. Why? I like to sort my tracklistings as Artist – Album – Track# – SongName. One problem I’ve always had with Mac stuff is that they assume they know what’s best for me. I know what’s best for ME. This is very annoying, and it makes me feel like a prisoner in my own system. I don’t see any reason why Song Name must be locked as the left-most column, so it makes me very angry. Hey Apple, why am I on lockdown?
• The taskbar doesn’t show the currently playing Artist/Track. So when I have Itunes playing in the background, and I hear a song and want to know who it is, I need to swith to Itunes to find out. This makes me less-than-productive when I’m trying to code or whatever as it forces me to stop what I’m doing and switch appplications.
• Similarly, with Itunes open, the currently-playing-track display only shows either Artist, Song Name, or Album Name, never a combination of the 3. I want the display to show “Artist – Album Name – Song Name,” but of course, that is not an option. To get the information I need, I have to click 3 times instead of just looking at the screen. Sure I can just look down at the playlist, but what if I’ve scrolled far far away from the currently playing track? Finding it again by scrolling is impossible in a 30GB library.
• It would be nice if applications kept the native UI. If I wanted a brushed metal UI I’d use OSX. But I am using WinXP and I expect my apps to look like they belong. I’ve always hated Mac’s widgets (eg: play buttons, volume slider pully things), and it bothers me that when the tables are turned and you’re running non-Mac software on OSX, you’re forced to use their native widgets. But I guess Winamp is the same (non-native UI), so this shouldn’t bother me too much.
• I’m very anal about my file nameing & directory structure, and for some reason Itunes gives me the uneasy feeling that it’s going to magically hijack all my stuff, rename files, re-order directories, and convert eveything to AAC. Perhaps it was all the promps on install asking me if I wanted to do all this stuff. LEAVE MY SHIT ALONE, and just play the freakin’ music.

Overall, Itunes feels more solid and stable than WinAmp, which is pleasant if you’re someone like me who is on their machine all day with MP3s playing. Itunes also wins with their superior ID3 support, as well as the superior playlist shuffling algorithm. The auto-volume adjustment is a godsend, as I was never able to find a suitable compressor/normalizer DSP plugin for Winamp. However, Itunes lacks in terms of customization, and what I would call obvious usability and interface design. This is the utmost ironic thing, because Mac, the supposed “superior user interface designers” fail miserably – and on the simplest of things!