There was a point where I thought I would keep all my CDs forever. When I lived in my studio apt with the walls lined with CDs, it was like a musical womb, where I could access any CD in just a few steps. When I got married and moved into a condo, suddenly it wasn't so convenient. I found myself moving from room to room a lot between the office, kitchen, living room and bedroom, which was difficult to have continuity in listening to a CD. I'd be in the bedroom at night and want to hear something, but just wouldn't bother, as I'd have to walk to the other end of the place, turning on lights as I go to dig up the CD. After researching for about a year, I settled on using the wireless Squeezebox setup and dbPoweramp for ripping to flac.
It took me about six months to rip my entire collection of 7,000 CDs. I had to buy a 6TB capacity NAS (4.5 usable space, just under 3TB used so far) and back it up at work, and it was totally worth it. CDs that collected dust for over a decade get played much more frequently now that they're plugged into playlists that I rotate between. I have my entire collection backed up at work, which is a nice feeling to be able to hear anything I want at my workplace that I spend more waking hours than home during the week. I use MediaMonkey for making playlists, then save to the Squeezeserver and re-index.
Now I can play my music in three rooms simultaneously if I want, and control with a remote anywhere in the house. I definitely listen to and enjoy more of my music more often because of that.