Of course this means most of my music is pirated (I tend to buy a physical album and then download a well-ripped or digital copy) but I've found it hard to move to other ways of managing my music.
My own way of organizing and collecting makes sense to me and pretty much no one else, but that's fine since hardly anyone else ever wants to use my computer to play music. I'll use Winamp until it is no longer possible to run on Windows, probably.
Still, pirated or not, I like having a space on my NAS for my traditional Music/Artist/Album/[track]_[title].mp3 folder structure. Pointing Winamp at it works fine for the majority of my listening at home.
Of course I've come a long way from running an unlicensed Shoutcast station in the early 2000's (it was nice having a friend who worked at a small hosting company who gave me the space to host the server and all the bandwidth I could need to stream to my massive audience of maybe 5 or 6 people at once ;)) but I still love listening to streaming "radio" in the car without any need for subscriptions or any hardware other than my phone. I've been doing it since I had a Palm Treo, but the move from a max data rate of ~256k/sec to LTE has certainly helped.
Only thing I really miss these days in Winamp is a way to cast to Chromecast/Chromecast audio in other parts of the house. Not sure if anyone's hacked together a plugin but I haven't really looked.
For anyone wondering what a good tool to organise your music like this is, for example if you use Winamp or something like MOC, it's a Python tool called "beets"[0] which will rename (or copy, if you choose) your files to a directory structure you specify. It will also talk to Musicbrainz to fill in missing metadata, and has plugins to fetch album art.
[0] http://beets.io/
People are gonna want collections - be it physical or digital - because that's what humans are like. If the music industry ever switched to streaming only, there'd be a MASSIVE decline in the industry.
I wish it was open sourced. That way we could fix the bugs and make sure it runs on newer operating systems.
But yeah... fun times.
Of course, these days I rely more on spotify and pandora, but the winamp streaming ability was always great, and it upset me when more online stations moved away from the generic, usable mp3 streams to more esoteric solutions.
Nowadays I use whatever is the Gnome default - Rhythmbox currently.