At our station, we have been moving to digital playback. We're a freeform college radio station with 2 hour block format shows. Every show picks their own music. Most DJ's have their own libraries and its about 60/40 computer/cd now. For personal libraries, we have a separate computer with Winamp installed, as well as iTunes, and another product called SoundByte.
For the station CD library, we started off by sending about 10,000 disc out to a service to be ripped. Pickled Productions out of Chicago was the company. After that, we purchased a CD robot and have been using DbPowerAmp for ripping. I've easily ripped another 10,000 CDs with that.
This brings me to playback. We decided to go with FLAC audio files for the LOSSLESS compression. Try finding a playback product that has 3 decks that will play FLAC.... they don't exist, or so we could find. A computer science student who was a station staffer at the time took up the challenge to write a program. It works well, for what we do, but lacks individual channels and control. If enough people were interested, I might be able to drag him out of his cave to start working on it again.
The initial blow-back from staff was pretty harsh. But once they realized that the station library being digital meant that they could actually find the music, and they didn't have to spend hours searching(or carrying a giant case), they've embraced it.
Moral of the story... yes, ripping that large library sucks. But you're going to have to do it eventually. PM me if you'd like more information.