One word - mastering. His CD is likely from the later (subpar) remasters. First (original) vinyl and CD pressings of DSotM and The Wall sound equally good on my Schiit/vinyl setups.
But I prefer my vinyl lately...and I can't point exactly why. There is something in it.
There is even more to the mastering issue that that.
I use a set group of test tracks to compare audio equipment for subtle differences, and both Dark Side of the Moon and Kind of Blue tracks are included. So, I've heard all the various versions of both of them, and my take is as follows:
I have long preferred the original mid-80s CD of DSotM to any subsequent issue.* But then I heard a vinyl rip of an original 1973 UK vinyl pressing by a vinyl ripping fanatic that calls himself "pbthal". Suddenly, it sounded like I remembered hearing it in the 70s. I compared the 1973 UK vinyl rip with vinyl rips of the original MFSL vinyl pressings, and the 73 is still better.
So, what I figured out is that DSotM was such a huge hit in the 1970s that - even if they only used the original two-track master to make copies for each country - US, Japan, Brazil, Netherlands, etc. etc. - the original master tapes wore and lost magnetism prior to the first CD and prior to the first audiophile vinyl.
Kind of Blue is the opposite. The original pressings all had 1/4 tone speed errors (a web search will provide details). But they did the sessions with a "safety copy" running in parallel, and when they unearthed the safeties in the 1990s, they were not only correct speed, but they were also in better shape due to being stored properly and never played.
Again, I've compared all the versions, and I currently prefer the "50th Anniversary CD" (before getting a Schiit Multibit, I preferred the 2007 SACD, but the Schiit does 16-bit, 44.1k so well that I can now hear a more natural sound on the 50th Ann CD.)
In general, when I compare vinyl rips of the same recent material to DSD/SACD and to PCM, my personal finding is that both vinyl and SACD add a very subtle noise that is pleasing to the ear, and thus sounds "better". This is called "euphonic" - a term often used to describe tube sound in the same way. So, I think that mastering makes far more difference, and for many 60s and 70s albums, the original master tapes deteriorated years ago (e.g. upon receiving the master tape for Close to the Edge, Steve Hoffman declared it dead).
(Please don't ask about a source for the vinyl rips - not only is it against the Forum rules, but my original sources are no longer online any more anyway. But I'm sure it is all out there on the Internet somewhere.)
And a big YMMV on all the above.
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* Actually, for DSotM, the definitive version is the Alan Parsons Quad Mix. In the early and mid-70s, Pink Floyd toured with a Quad sound system with giant speaker stacks at the rear of the auditorium. There are certain sounds in DSotM that make no sense - they just seem silly - until you hear the quad mix where they move around the room. Unfortunately, the DSotM SACD used a new mix that was ambient surround. And Parsons was heavily involved in DSotM as an album, so hearing another engineer's later version is not the same. The 2011 "Immersion Blu-Ray" has the original Alan Parsons Quad Mix. Having said all that, I rarely bother to sit in the living room sweet spot with the surround speakers and listen to Quad albums, and so I am usually listening to the Stereo Mix...
