I agree with most you posted, good post.
Most don't seek Hi Fidelity, in fact most use ear buds and low bit mp3.

Entertaining music does not have to be Hi Fidelity, but I prefer that, less can irritate me unles the beer is cold.
You mention digital and analog devices. To hear any real difference, a Hi Fidelity system is required. Not one good item but a system. Most are not interested enough in tunes to acquire that. You can't just go to a store and buy a system. It takes hands(ears) on and time to assemble a decent system. The cheapest way to better audio is a decent pair of headphones and a decent player, say around $1k for both. I prefer speakers.

I have over 1K "OLD vinyl". My Beatles collection may be worth more than my house. My favorite LPs are my TAMS albums. I have a lot of old ROCK and a lot of JAZZ.

One difference "back then" was "stereo" which is rarely pressed or recorded now. Stereo is not the end all, but is entertaining. Mono can sound good, as can the mix done today. In the day most albums were recorded in mono.
Most old LPs were recorded to analog tape, many of those tapes still exist. A really fun example of a remix is Paul McCartney doing a remix 33 years later of Phil Spector's album 'LET IT BE'.

One deal with vynl is you MUST have a record cleaner (vacuum is best). Some cost thousands, mine is only about $500. Even a new out of the wrapper record sounds better after washing. You must have a record cleaner if you play LPs.

I agree that an LP over a decent system sounds better than a CD in the same system, but a CD or digital file can also sound excellent. A casual listener would hear no difference.

Back "when" all amps were tube. Then all became solid state. Now tubes are the "IN" thing.
I have tube amps, tube preamps, tube phono amps. I like them. They look great! I also have solid state.
For most solid state is the best choice. It is cheaper and sounds great. At the same volume, most will hear no difference.
I could never afford enough tubes to open up my main speakers. At 4ohms run 2400 watts to each.
Less demanding speakers can sound great with a 2X20 watt tube amp.
One trade off is to mix using solid state amps and tube preamps.

One thing as to tubes is guys who swear by NOS tubes (old rare crap). I have many friends who do. I don't . I believe a well made tube does not need to be from WW11. You can pay thousands for a set of old rare tubes or less for modern well made tubes. "Tube rolling" is a hobby in itself for many. I believe the placebo effect is going on with much of this.

One thing not covered so far is the DAC (digital to analog converter). 99% play digital tunes. A huge deal as to sound is converting the digital back to analog. A DAC can be cheap, the $20 tune player from Walmart has one inside. Some audiophiles pay $10K for one. For better digital playback, you need the best DAC you can afford. The good thing is you now get a lot more bang for your buck than even 5 years ago. The DAC on my porch I am with now retailed at $1800 ten years ago. Equal or better now is maybe $500.

No one piece of gear will give you great sound. The deal is to improve the weakest link in your system. Find speakers you like to hear and start from there. Speakers are the big deal.
Most people can improve their present system a lot with no $$ added just by learning how to set it up.
https://www.youtube.com/watch?v=BOrZEreKB8Q