First off, nothing beats being in the band or orchestra in the middle of the music. The original goal of "Hi-Fi" was to get as close as possible to a live performance. Vinyl was good, but not as good as reel-to-reel tape. But, the bottleneck was always playback. That's where cost made the biggest difference.
You need/ed a low-distortion amplifier, and probably a pre--amp, equalizer, and a power amp. In the early 60s, the amps were all tube jobs too. So, you'd actually have to replace burnt out tubes as if they were light bulbs. Moreover, if you used tape, the sound quality would deteriorate a bit with each playing. It was a similar problem with vinyl.
So, if you wanted state-of-the-art audio equipment, you had to shell out a lot of cash. Well, personally, I built my own Dynakit and Heathkit. Check ebay; and they're selling Dynaco Dynakits for big bucks today. And, then there were the speakers, and everyone wanted the closest they could get to studio monitors.
At any rate, playing vinyl was third rate in terms of sound quality, costly, and time consuming. But, while all this was happening, most people were not audiophiles and were listening to rock and roll on tinny transistor radios. In popular music, there wasn't even much concern about "stereo" or "stereophonic" sound. "Pet Sounds," Hendrix and the later Beatles changed all that. By the early 70s, people were listening much more closely to the music. Vinyl still wore out, though. And transistors replaced tubes. Soon, many people listened to cassette tapes of music recorded in the studio. Then came the cd in the 80s.
The advantage of digital is that the media is cheap, and if it's recorded directly at the studio or performance --as opposed to remastering previously recorded material-- it'll be at least as faithful to the original as vinyl. The only way to compare, imo, would be to make analog and digital recordings of the same live performance (in studio or out), and then use the same playback equipment. Even then, imo, it would still take someone with a fantastic ear to tell the difference. I would be surprised if it were possible.
When people talk about the sound difference between vinyl and cd, they're really indicating a preference. I, too, like the warm sound of a vinyl record played on a tube amp. It is definitely different, and would be much more nostalgic. Not always for good reasons, either. If you bought Motown 45s or lps, you remember that almost all of them would have scratches and pops after the first few plays.
There are records I recall that just won't sound the same with the defects.
Do I think it's worth the trouble of playing vinyl? I have to say not for me. I'm even quite sure that I can't hear as well as I did. If I want hi-fi, I go to a concert or jazz club. I will probably convert my vinyl to digital, just for convenience sake. Maybe I will sell some of my old records after I digitize them. Now, the question then is which format to use (ogg, flac, etc). It's probably be flac.
"A man is rich when he has time and freewill. How he chooses to invest both will determine the return on his investment."