[seanp2k2]

If, by painful, you mean “the need to plug in that old HDD with 100k MP3s”, keep up ratio on private trackers, and end up finding tons of amazing music again, all completely free to do anything I want with, then sure :)

Squeezebox Server was awesome, and these days it’s way easier and more accessible to host a media server and playback in ways you want.

[Al-Khwarizmi]

The pain, for me at least, was in organizing all that music. I ended up with a mess of files and folders, people didn't use ID3 tags consistently (if at all) and if you need to add them yourself manually then yeah, it's a pain...