The muddy waters of Analogue vs. digital today

With new technology, everything is changing so fast it is hard to keep up with new recordings. I have had a turntable all of my audiophile life, although I admit I played mostly CDs for many years. It was only since I upgraded my analogue system to a certain degree in the mid-nineties, that I could hear that records sounded better than CDs. It wasn’t a very expensive upgrade, a used Rega 3 with glass platter, new Sumiko Bluepoint Special, and a floor demo ARC PH-3. Probably somewhere around $3K. Mid-90s remember.

Now my system is very upgraded and I can hear more differences between vinyl and streaming at high resolution. CDs have kind of been left in the dust. 44.1 resolution sounds kind of tinny and flat. I listen if that’s my only choice, but I can easily hear the difference. I credit myself with a decent ear after doing critial listening for 30+ years. My ear is not as good as most reviewers, but you'll understand why it’s good enough to write a forward to this thread.

I won’t go through the differences I hear between analogue and digital, because you’ve heard it all before. What I want to talk about is my confusion in this new recording landscape. 

I had purchased Roberta Flack’s "First Take" when it came out and I’d kept the record for more than forty years when I realized it had really seen its better days. Basically, it was unlistenable, even after a few washes in the Degritter. I looked at near mint copies of the record and they were quite expensive. Then I saw that there was a new pressing for a reasonable price.

I was listening to the new pressing of "First Take" a few days ago when I realized it sounded overly compressed at the high end. I asked my new audiophile friend chatgpt if the record was pressed from an analogue source. Nope. I was basically listening to a digital recording pressed into vinyl. Chatgpt says that most records made after 1980 come from digital sources. So, I found a reasonablly priced orignal pressing of "First Take." My grandaugher in college can have the digital one.

Today I was playing a fairly new recording of Gustavo Dudamel and Yuja Wang playing Rachmaninoff’s Variations on a Theme by Paganini. I live in L.A. and have been lucky enough to see Dudamel live many times and Yuga Wang several times. It’s a beautiful recording, wide and deep and detailed and musical. I pronounced it the best classical recording I owned. But it was put out recently. So, I checked with my audiophile buddy chatgpt. The record is from a very high resolution digital source. Chatgpt says that digital can sound more analogue on vinyl because the engineers roll off the high end a bit.

So, now things are more than a bit confusing. Do I buy a recording from before the 80’s on expensive vinyl or might it actually sound better streaming at 192 kHz? If you listen to Patricia Barber’s "Clique" at 172 kHz, it sounds pretty good. So good, i have not bothered to go out and buy it on vinyl.

Does anyone else feel a similar confusion in this modern market, and do you have any suggestions for negotiating it?