I have read somewhere that at rarified levels, analog and digital sounds converge and tend to sound quite similar. One is not better than the other - just different presentations of the same truth.
The choice then is more of personal preference. I guess it is a bit like top end tube and solid state amplifications sounding similar than different.
Having only had the opportunity to listen to a few top end digital, I would love to be able hear a top end analog rig, but alas it is nowhere in sight.
I am sure digital technology for music reproduction would have progressed a lot if "high fidelity" was one of the main criteria for the consumers, but I dont see that to be the case. The reason is obvious, after all only a handful really care about quality of sound, most others are after quantity, convenience, cost and availability, so that is the area where things have progressed.
Take example of photography. Digital photography has progressed so much because there tons of people who are ready to pay for quality. DSLR is a household thing in developed countries. People splurge on photography on occasions and ceremonies. The same can be said about AV, people are ready for large screen TVs, HD home theatres hence things are rapidly and in real sense moving forward. Nobody cares for VHS tape.
Jls, the point is, in audio unfortunately digital is still far behind analog at highest level on sheer quality front.