Hey Spencer - thanks for the vote of confidence. I'm sure there must be scientific reasons for what I'm hearing and likely they're buried in the ripping software.
My friend, whose system I've enjoyed over many years now, and where I've done lots of interesting comparisons, has a really nice analog rig (Teres/Shelter/Origin/Einstein). Just recently I brought my MW Transporter over there and we listened over a weekend, mostly comparing preamps and digital front ends (all very nice stuff too including the MW TP and Empirical PaceCar and Electrocompaniet player), throwing in his vinyl rig every now and then. I have to say that I still prefer vinyl - BUT that the margins are becoming narrower and narrower every time I've had the opportunity to make such comparisons. This, in spite of all the file ripping foibles mentioned here, given that all the PC files we were listening to had been ripped in iTunes to either AL or WAV or AIFF. I'm not suggesting you give up your analog, and I agree, there's lots to sort out in PC Audio. OTOH There is a whole lot to be desired for having an entire library of music at your fingertips that you can mix and match at will though without hesitations. It's definitely worth a listen to what's out there these days - you may be very pleasantly surprised that the margins of difference can be surprisingly narrow, with plenty to be enjoyed in both arenas.