Schubert, Ripping CDs doesn't have to be a tedious job. Just set up the server and when you feel like listening to something place CD in the computer and start ripping. Few minutes later first ripped track will appear in your playback program and you can start listening to whole CD without interruption (since ripping is faster than listening). That way the only difference from what you're doing right now will be placing CDs in computer instead of CDP plus few additional mouse clicks. CDs, that you listen to less often, will be ripped last, but CDs that you enjoy the most will be ripped first. Listening to them again from the server will give you a break from ripping. That way I ripped slowly similar number of CDs. The only time consuming might be finding artwork of the less common CDs.
I believe in preserving original CD. I rip into ALAC to save space (0.6TB so far), but any other lossless format is OK (batch converting formats is easy). I keep copy of my music library on two additional 1TB HD. I feel I need two copies because something might go wrong during copying (that can damage both HD) and I feel safer keeping one copy outside of the house (in case of fire, theft etc.). I update only one of them after adding 5-10 CDs. That way, in the worst case, I will have to re-rip only max 10 CDs.
Do not toss CDs - just get rid of the cases and put them in a large box.
Ripping program is another issue. You need program that will do exact copy. I use XLD (free) for MAC, but for Windows I would use EAC (Exact Audio Copy) - also free.
