This is a touchy subject.
The way I see it: if, at the time of recording, the mix was recorded to an analog medium, then I want to hear it in analog. The same goes for digital (for the most part)...
So, if the recording engineer mixes everything down to DSD... I want to hear that album in it's original format.
If it was recorded to tape, I want to hear it on tape, or the next best thing, a vinyl record that was cut by a competent mastering engineer to a lacquer, using an all-analog signal chain and pressed at a good pressing plant like QRP, RTI, etc...
There are companies out there right now that are putting out the best sounding reissues on the market. Analogue Productions, Music Matters, even Blue Note directly with their new Tone Poet series are releasing these recordings on vinyl and they can beat out ANY digital reissue of the same release.
I know the big labels are trying to preserve all of those old master tapes that degrade every time they hit a tape head. But some, NOT ALL, of these labels are using cheap A/D converters to record down to 24/96, 24/192, 32/384 etc, instead of cutting new lacquers from the tape. As we all know, lacquers degrade over time... it's a conundrum.
90% of these new vinyl reissues that are being mass-produced by crappy pressing plants, hitting the shelves of Barnes & Noble, Best Buy, Walmart, Guitar Center and your local record stores, with lacquers cut from a digital recording of an analog source... just don't cut it for me. A simple, blind, A/B test on a good system will reveal that. Obviously, the mastering, pressing plant, all play a big part in that final product.
With all of that said, you can find some incredible DSD recordings of analog masters that, depending on the hardware the studio uses and the hardware in your system, can get you as close to that master tape as possible.
I like, and use, both digital and analog sources in my system. But if I had to choose one.........