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While Plex supports both audio and video, you can't cache media locally on devices with Plex without paying $5/mo for a Plex Pass so your concerns about our remote connection will come into play more. If this is more for music you can use Subsonic or Airsonic instead and spend much less/nothing to have local caching and a greater choice in playback apps.

Winamp - it really whips the llama's ass!

Not sure about everyone else but for me what replaced winamp was mpd with ncmpcpp on my desktop and laptop and Google Music on mobile. This let's me access my library either locally with mpd clients or remotely by pushing it all to Google Music and using their player.

I haven't really used winamp since the early to mid 2000s. That's when the iPod hit and then I used Songbird which USED to be able to sync media to your iPod. Then I jumped from that to Google Music around 2011 and mpd for local access at home. If Google decides to "pull a Reader" and discontinue Google Music I'd probably switch to Subsonic (good mobile apps) or Shoutcast or something.

Subsonic fulfils all my needs (mostly audio), and has a fine Android app (also iOS but I've never seen that one), a nice-looking, built-in web app, and is supported by other third-party music players (I use Clementine).

http://www.subsonic.org/

I know you asked for a "device", but if you have a net-enabled device that can run Java, this is a pretty solid option. It was easy to set up (unlike Ampache, which I tried which was pretty useless). YMMV

Check out Subsonic.

If I had TMo, could I sign up my own Subsonic streaming service, and access it for free?

Being able to access your collection from multiple devices from anywhere with an internet connection is the major draw of Subsonic . I'm still trying it out and deciding if it's awesome or just kinda cool, but so far I'm liking not having to upload everything to the cloud first.

There. Fixed that for you.

Or, try the wonderful subsonic music streamer instead!

It's a great piece of software (server-side) with a sweet android client (all GPLv3). Also has many other clients (iOS, flex, windows7, etc).

I have a pogoplug but was not particularly impressed with it. The main problem was that it was super slow. I don't know if it was just my ISP or if it's routing everything through pogoplug servers (I'd heard the latter) but I'd be lucky to get 30kbs on it from a computer on the other side of the city. The other problem is it has (or at least had) a bunch of bugs in it, and the web interface was brutal.
I replaced it with a $100 desktop i bought from the recycling depot and run an FTP and subsonic on it for hosting music. I find this much more effective than the pogoplug was, although maybe if I'd had more patience I could have gotten it to work better. It also allowed me to install tversity to stream movies to my play station. They aren't FOSS, but they are free and I'm very happy with subsonic and tversity so far.

Why store all your music in "the cloud" when you can serve it yourself to any browser and many devices (iphone, android, etc) from a PC you control using Subsonic?

Try Subsonic.

I recently discovered the joys of Subsonic; I have the Android client installed on my phone, and the iSub client on my iPod and the Subsonic server running on an old system at home. I now have a single repository for all of my music that I can access pretty much 100% of the time - if I know I'll be listening to, say, some Penguin Cafe Orchestra during the day I can select the album in the Android client and download it straight to the phone over my local WiFi before leaving home in about five seconds flat - I can even set the client to force the server to resample the files to a maximum bitrate if I'm connected via 3G. All of this means I can access whichever album/track I want to listen to out of my 500Gb (and growing) collection and store it in one place.

This is a smoking gun to any pirated or "borrowed" music in your collection. Let the subpoenas begin! Or, you can leave the music at home and use something like Subsonic, which provides almost all the functionality of GMusic ... the client just needs some love and polish.

So basically it's Subsonic for normal people.

Yep. I used it for a long time and it was pretty good. I was very pissed of when it was killed off, not least because it wasn't a free app. OK, it's not like I paid a fortune for it, but still... Anyway, I have since switched to Subsonic and it's working a treat.

Just migrate to Subsonic. Much better imnsho.