One of the reasons I gave away most of my cd's was the engineer who mixed the cd used either compression and/or did not allow the original mix to shine through. Michael Fremer at Stereophile/Analog planet has done an exhaustive amount of research on this and I'm sure the reason why all but only the best cd's are inferior to the original LP and the analog master tapes is out there. I am certainly no expert but from what I have heard, a cd mix, even if its from the master tape directly, is subject the mixing engineers opinion as to what sounds good. If it's not true to the master tape/LP, then it's not for me. This is why I am gearing up to sample a dupe of a master tape. Those who have had the good fortune to own or sample one of these tapes have raved about the dynamic range.
As far as using my (pro or semi pro) Otari or Technics (after refurbishment) decks to record a compilation tape from LP and/or hi res music files, I plan on doing the same, mainly for the convenience. I have recorded hi res (Flac,DSD) music files from one of 3 stand-alone hard drives (total size of the all files, approx 6 tb) via my Asus laptop running Jriver music player through the integrated DAC within my moderately priced Marantz PM7005 to my TEAC X-1000R and when switching from Tape to Source, I can hear virtually no difference in sound quality.. and this through my "B" system. I expect even better results when I do the same via my "A" system: Otari MX5050Bii2, soon to arrive Yamaha A-S2100 Solid State integrate amp, BMC PureDac and GoldenEar Triton 1 speakers.
I know this appears somewhat academic to many, especially to those considering re-entering the R2R genre, but I find it is great fun determining what provides the best sound through my system.
Finally, a nod to all those contributing to this conversation... most of you know far more than I do about the subject, and I am enjoying the real and theoretical knowledge presentation.