Bob -
I'm a contemporary age-wise. The way I got unconfused about setting up a digital library was to just jump in and try it. I tend to take a pretty basic and pragmatic approach to most things audio - which is to say, I don't obsess about audio quality differences that others talk about if I can't hear 'em (e.g., WAV vs ALAC). AND I tend to prefer lower cost solutions that provide 90% of a benefit rather than way more costly alternatives that will realize the last 10% or so. I'm probably not your poster child for "audiophilia" as defined by some. Consider my comments representing the "low tech" end of an implementation continuum.
I use a MacBook Air and iTunes to rip CDs in ALAC to a pair of Western Digital 2TB Hard Drives (one is back up to the other). iTunes gets criticized mainly (I think) due to association with lossy, compressed, and crappy sounding MP-3 files (I CAN hear that difference, by the way!) But it doesn't have to be that way. There are preference options to ensure good quality rips. iTunes is very fast at ripping CDs (even w/quality parameters max'd out in preferences) and I like the way it handles meta data. It works consistently. No glitches or mysterious software issues on my MBA.
I use BitPerfect v3.0.1 for playback. I have a double headed USB cable (one leg for power; one leg for signal) that I connect to a Gungnir DAC via V-Link 192 with a Stereovox SPDIF cable. The Gungnir feeds into my integrated amp or pre-amp depending on what equipment I'm running.
I'm sure my relatively low cost/low tech approach can be criticized as "non-optimal". All I can say is, it works reliably and things sound very good. I guess it's jitter reduction, but to my ear the sound from ripped CDs vs actual playback in a CDP seems smoother and more relaxed (and I don't mean due to changes in frequency response). Good luck in your research and final decision.