Now I get it...

Jerry, I am an analog guy since the early 1970s.  I play CD in my car (and I do have a bad-ass car audio system) but probably will get streaming and a quality DAC next year.  I have bought a variety of high quality audio systems over the years and for the past 1 1/2 years have been creating the best system of my life.  I recently added a new Rega Planar 10 and a Lyra Delos phono cartridge (rather then the Rega cartridge) and it far surpasses the performance of my last deck.  I am quite certain the Manley Chinook phono stage and my BAT preamp & amp play a tremendous role in it all, as does the upper-end Audioquest signal cables, power cables, speaker cable, and power conditioner.  A system is just that, a system.  Mating some nicely matched components delivers a wonderful experience. The joy of vinyl is really quite something special.  When you sit in "the sweet spot" and just about fall into the music, and it's very 3-dimensional, almost holographic, there is nothing like it.  I have never heard streaming music do that.  Maybe it is capable, but I have not yet received that demonstration.  Steve Hoffman forums are very helpful on the subject of SQ for your particular albums of search, no doubt.  I will disagree with tablejocky, though, about avoiding reissues.  There are plenty that are a waste of money, no doubt about that.  But, there are so many that are spectacular and will provide that magical moment for you.  Just a few examples; Stevie Ray Vaughan, In Step (Analogue Productions and Quality Record Pressings), Paul Simon, Graceland (25th Anniversary Edition and RTI pressing), Carole King, Tapestry (Mobile fidelity Original Master Recording), Joni Mitchel, Blue, Jeff Beck, Blow By Blow (Analogue Productions and Quality Record Pressings, 45 RPM). 

There are so many more that sound so incredible, they can bring tears to your eyes.
Enjoy the journey and welcome to the wonderful world of vinyl.

Sometimes bad recordings can have endearing qualities that you will eventually recognize.

I wonder if you can purchase a more forgiving “musical” cartridge for poorer recordings?  

Consider ultrasonic cleaner if you have not already. Especially if you bargain bin and listen to older records. You'd be surprised how much ground dust accumulates in 40-60 years. Though that dust could tell some pretty cool party stories.

Congratulations.
I have done the same thing resently. But in a much smaller scale. And it goes in waves.
I have done most of the things I could do in the vinyl playback chain. And that is a lot over several years (!).
I almost gave up. The magic were there and were gone and now it is back in full effect.
To illustrate what I have done to get there:
Löfgren B Arc protractor
Dynamic adjustment and by ear SRA
Peter S anti-scating procedure
Speed adjustment while playing
Good ML stylus and cartridge(s)
Redraw tonearm cables with pure silver wire
Replaced RCA cables with known uF fully shielded
Upgrading dedicated power supplies
3 different RIAA Amps tested
Passive pre amp with coils
Build my own power amplifiers (driven by car battery)
Pure silver dual shielded ala chord DYI speaker wire
Bookshelves upgraded with top of the line crossover components
And dual 8" sealed sub
Dedicated room with sub 300ms decay times
Treated reflections points
Base traps
All lined up perfectly to the wall boundaries

Now I lend my RIAA to a friend. I had another RIAA in the meantime that the op-amps I had upgraded to audiophile grade developed for hi-fi MUSES 01. That were superior too the original 
OPA2111KP.

But here is the catch.. I ordered fully descret op-amps to try them out. And surprise they were better than the MUSES! And the they played one octave lower than the MUSES couldn't.
But they also made vinyl playback so much more enjoyable like your experience. 

So I have not powered on my new streamer and DAC yet since then.. and just enjoy my vinyl collection for the moment.

And it took all those years as in a roller coaster to get too this point..