I usually prefer CDs from the 80s, before they were "remastered", dynamically compressed, etc.
How do you feel about more recent re-masters where they have been more sensitive to over-compression and in some cases re-re-mastered to address the appalling re-masters? I have some issue with re-masters that attempt to fix problems with the source material. I'm not a huge fan of artists tinkering with the original material, adding elements that got lost in the mix due to overdubs/noise, were not technically possible, or just re-mixing for their taste. At least Taylor Swift is up-front about re-recording her albums.
My gut is that music recorded/mastered to tape is going to sound 'as intended' on vinyl and everything recorded digitally (the old DDD label on CDs) targeted CD. I have nothing scientific to back that up though.
I don't trust them enough to risk spending money on more re-masters. I always go for the original.
Interestingly, I've grown to dislike music that is too perfectly produced. I like that the singing isn't perfect, there's some background noise picked up by the mikes, etc.
For example, listen to some of the Jefferson Airplane albums from the 60s. Those albums would never be produced today, because the band is a bit of a mess. The harmonies are out of sync, the pitch is imperfect, the timing erratic, everything is off kilter. But that rawness is, strangely enough, what makes the albums so endearing and a treasure. It's like the band has come by your house and is just having fun in your living room.
So much better than the antiseptically perfect modern productions, along with that awful ubiquitous autotuning. Barf. C'mon, dare to have a sour note here and there.
Eminem's very early music feels amateurish, you can hear various audio issues. But it's some of its best work.
Now, anyone who makes an album can make something. That sounds absolutely spotless with about $2,000 worth of gear. Something's lost, there's something nice about hearing a mistake someone makes, but they don't have enough money to rerecord it so it stays on the record.
Rarely when I make my own music, I'll just leave some of the problems in there.
https://youtu.be/KLjvfqnD0ws is one that has been digitally cleaned up but prefer listening to the messy version sometimes
See "The Wrecking Crew" documentary.
Even for "Herb Alpert and the Tijuana Brass" there was no "Tijuana Brass". Herb was a session musician and decided he'd try making his own album. It was such a hit he had to go round up some brass players so he could tour.
This was eventually fixed and proper CD masters started to become common in the early 90's.
Another thing to consider is the natural aging of our ears. Even without abuse high frequency sensitivity degrades as we get older. Those 80's CD's probably don't sound as harsh to someone 40+ today as they did back then.
The only issue I have run into is using really cheap CD players. Some of the earliest CD's were manufactured using sub-optimal material and manufacturing processes and have always had a very slight warp to them even from the day I bought them. The really cheap CD players most notably Wonnie have trouble compensating for this.