I have used it for all these years because it "just works". I have 2 needs in a music player - play whatever I have locally, and stream me something different when I want to. Winamp did both of those, and I never had an issue with it.
It is hard to "surpass" something that meets my needs perfectly and has given me no issues for over 10 years.
The main reason I use Winamp is because it has global keyboard shortcuts for controlling playback. I'm not sure if any other media players have that, if anyone knows of one that does I would love to know.
Out of curiosity: I use AHK to do basic testing automation for a windows application that I have literally zero ability to control programatically (to achieve actually good automated testing). Anyone have a better option for this kind of use case?
I wrote some software (http://www.mute.fm/) that controls playback for you automatically when you watch a video (it will pause/mute it and resume it afterward.) It also lets you set up global hotkeys.
Yeah, I used to use VLC for playing video files, but man it takes a lot of memory and when it decides to "cache fonts" (or something like that) it takes literally hours to start.
Now I prefer smplayer for videos and foobar for music. Although I've been a heavy Rdio user for some time.
VLC can do many neat things, but I never, ever saw it as a replacement for Winamp. It's more like a toolkit, or at least the multi-tool you fall back on to do a variety of things.
I don't have any demographic information to share. But I personally attempt to rate my files. It gives a nice way to categorize by quality. That way I can have abjectly terrible music in my collection, but filter it out for the purposes of not ever wanting to listen to it.