Comment iPod Touch + MPD + WiFi (Score 2, Informative) 110
Well, the "article" is a bit of disappointment, however I've been in the same situation and here is how I approach the problem (way more music then will fit on my 8GB touch or smartphone): I have a linux server (Dell Studio Hybrid running Gentoo) that I always leave on which has a copy of my music repository. On it I run Music Player Daemon (MPD) with Icecast as one of the outputs. I connect to MPD via a simple web client (there are several: http://mpd.wikia.com/wiki/Clients) from my touch, build my playlist, then point Safari to my Icecast server's IP/port which opens the media player and I can listen to MPD anywhere I have WiFi. I'm not sure what the minimum bandwidth required is, but even my smartphones (previously Samsung Saga on WM 6.1, now Droid Eris running 2.1) work with this system. For the record I used TCPMP on WM 6.1 (Windows Media Player mobile worked too, but that app is horrible) and now use I use A Online Radio for the Droid (oddly enough, the built in media player on Android doesn't do streams and it's touch to find an Android streaming client that let's you specify any address/port you want).