What in the world is going on.....

At $75K I would assume that your signal chain is higher res than average. Also, since the LP playback is the outlier, perhaps there is some incompatibility between your stylus and the cutter head, or maybe you need to play with SRA, azimuth, VTF, etc. If your tonearm doesn't have adjustable VTA, it could be as simple as adding a thin turntable mat on top of your usual one. It's generally known that one can get a somewhat richer, lusher sound with a *slightly* tilted back tonearm.

OP-

on a highly resolving system upwards of $100K, you will hear the best/worst in recordings, warts and all...

I noted that with most of modern pressings there are lots of manufacturing defects that I had to deal with by sending copies back to receive replacement. I once had to send back whole batch of poorly mastered and sounding records where the bass diminished all other notes to almost inaudible. I guess certain current releases are better-of stickin' to MP3 or other similar cwap.

Roy Halee was the engineer I believe. He did the mixes on this album. 

This from Wikipedia:  Simon also worked with longtime friend Roy Halee, who is listed as co-producer on the album. Halee, who had retired years earlier, was mostly recruited to advise on how to create natural echo. He was unfamiliar with Pro Tools, so Simon helped him with it. "I always liked working with him more than anyone else," Simon noted

His early solo albums--standard issue-- sound pretty great as I remember. Don’t know if they were all Phil Ramone, but that would explain a lot. I have more respect for him now than I did back in the day--it was too "pop" oriented for me at the time. I got to hear him play several years ago at a small benefit show in a non-music venue-- audience of several hundred people. He was unbelievably musical.

I can't say anything other than this particular record is not his best - So Beautiful So What is, IMHO, a far better album. 

I agree with the observations about its sonics - there's a marked difference between the two 

Do not have this CD but other recent Paul Simon CD I do have was definitely mastered to be "loud".

Have you not noticed how loud this album is? Usually that is a sure sign of heavy handed compression. I'm going to make a digital transfer and will check the wav file. My guess is that I'll see plenty 9f chopped off peaks.

I'm sorry that you are disappointed in the vinyl version of the new Paul Simon record, "Stranger to Stranger." I bought the CD the day it came out and played it in the car on the way home, and played it again listening to headphones later that day. I like it! So, just ignore the poor quality of the vinyl and buy the CD. After all, we're in it for the music, right?

The first sign that the recording was at least mastered, if not recorded digitally is the download card that accompanies the record. Not that all digital is bad- I have some wonderful sounding records on vinyl that were natively recorded in digital; indeed, a lot of stuff since the ’80s was recorded digitally. Remasters are a different story- the difference between an old analog record and a digital remaster is often noticeable, but in some cases, like some of the Steve Wilson remixes, the trade off of a better mix (e.g. Aqualung) is worth the price of admission, particularly if the original analog recording isn’t very good.

As to why this record sounds lousy on your "big" system, it could be that little care was taken in mastering it to vinyl. Or perhaps it isn’t a very good recording to begin with. I don’t know enough about the record, haven’t heard it, and don’t even know who mastered it. What sounds good over an MP3 is very different than what sounds good over a wideband playback system. (Think back to the days when pop records were created to sound punchy on the car radio - some sound great over a good hi-fi rig, but some are really dead and lifeless sounding). My suspicion is, another copy isn’t going to sound better, but if there are others who have this pressing, they can chime in.

I can give a somewhat similar example, comparing cd and youtube.
Yngwie Malmsteen with Japanese orchestra. Great music. First, I listened to it on youtube through Grado phones, no external dac, and it sounded acceptable. Then I got the cd and it sounded terrible on my rig, I threw the cd away. Somehow they managed to completely screw up that cd, I don't know how. My expectations were not high, yet I couldn't really tolerate that crap. Still listen to it on youtube.

I suppose, hew is correct about mass market production, but I don't think it fully explains the lousy sound from high end rig. There is something else to it. Bad pressing? Dirty record? High expectations?

I thought I was the only one who really didn't like this album.  Guess not, but Fremer sure creamed all over it.

http://www.analogplanet.com/content/simon-and-halee-reunited-again-make-musical-and-sonic-magic

I bought this album when it came out and posted a comment on it and did not receive one response. I felt that it was recorded hot, had sibilance issues and seemed compressed. I bough the vinyl. IMO, the song writing is disjointed and the lyrics seems forced. There are some interesting moments and probably worth  purchasing but not near his best effort. And, I am a big fan of his music!

Simple explanation is that most commercial recordings are mastered to sound great on lesser systems. High rez systems will make all those recordings sound like crap. Unmastered albums is actually a thing now.

I listen to various quality recordings with both speakers and headphones and good amplification.  

Headphones tend to not have as much imaging and soundstage so I find the difference between very good and average recordings in that regard to not be as big with headphones.    

Or it is quite possible that mp3 done well can be higher quality than vinyl not done so well for whatever reason.

So technology alone seldom dictates what sounds best.