Mapman - what follows is a copy and paste of some of the research I did and posted on my system thread on Loudness Wars. you might recall seeing it?
Due to the unfinished state of virtual systems I am not able to link it, so I copy part of it here as I feel it is relevant to your thread.
I spoke with Maegan Ritchat of Lacquer Channel a couple of times last year about this to get some answers about Loudness Wars and the real differences I hear between Vinyl and Cd.
http://lacquerchannel.com/the-engineers/maeghan-Ritchat/ Lacquer Channel is one of the largest mastering studios in Canada.
translated from my conversation with Maegan.
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When the vinyl is cut from a digital master the engineer must TONE THIS DIGITAL MASTER LOUDNESS FACTOR DOWN. He/she has no choice on this because of actual physical limitations with the cut grooves on the record, and noise itself.
For example.
If the band is bass heavy like a rock or reggae band, the bass may need to be filtered at 40 hz, or put into mono below 40 hz. This prevents the grooves from being cut too wide (<------->) and even running into one another. One of the factors deciding this is how long the songs run on the vinyl side being cut. On the high frequency end depending on how SSSSShhhhh or how Tizzy the digital file sounds; if it was captured sounding a little harsh, a 16k filter can be used as one option with the vinyl. Just one reason vinyl may sound a little more rolled off, smoother, compared to its digital equivalent on some records.
The end result is a less fatiguing sound with vinyl, once this "loudness" has been toned down. Maegan said in her experiences to date with customers who have heard digital and vinyl from redbook CD level source files on resolving systems...customers generally prefer the vinyl.
So a couple reasons above why the sound differs between the vinyl and cd, even though the digital master might have been done at 44,1k Hz 16 bits the red book cd standard. Now if the Digital master file is higher than the CD standard 44,1khz. 16 bits
This leads to...
the second finding and Higher Rez files.
When Higher Rez Digital files are available like 96khz/24 bit or higher - it makes sense to use them and these are indeed usually used for the vinyl cut. So when you buy the vinyl you are probably getting the LP's made from the higher rez files if available. Maegan confirmed this. This however would need to be confirmed on a per LP basis with the mastering studio involved.
The genre makes a difference from a general perspective. She agreed that Classical, Opera and Jazz for example are in general terms, better files to begin with, in that they are more dynamic than your typical rock, pop group digital masters which have more loudness factor and compression.