@krelldreams
Let me see if I can summarize the last 40 years.
I bought a high end CD player when they came out and upgraded every few years, Nakamichi, Sony, Sonic Frontiers (tube CD player… 1995?). I traveled with CD players and headphone amps during the mid to late 90’s. I traveled internationally a lot. Then in in about 2002 started an office system with headphones and a iPod… then added portable DAC… headphone amp… PC… with different software… River… then a real DAC ($3.5K… in 2010). Then my home system added an $18K Sim Moon CD/DAC… around 2010)… streamed using a MacBook… unplugged so running on battery… shut down extra processes. Vinyl alway was soooo. Much better. I would channel surf ripped music… just not satisfying.
I bought an Aurlic Aries G2 streamer ~ 2018. Huge jump in sound quality. Finally, it was actually in the same world as vinyl. Still disappointing… but not terrible, as before… flat, trebly… anemic. Then I upgraded my streamer to an Aurender N100… way better than the Aurlic… then tried a Aurrender N10… much better… and bought a Aurender W20SE. Honestly, holy cow… finally we are talking real music.
The last really significant step was swapping my DAC to an Audio Research CD9SE… this finally raised the performance above my contemporary Linn LP12 ( Akurate… mid level, with a $3K+ isolation platform) with an Audio Research Reference 3 phono stage. Finally, digital was completely engaging. Tonally, sound stage, imaging… everything. What an odyssey. I also, had a Berkeley Alpha Reference DAC ($22K) in my system for several weeks. To my surprise the ARC REF CD9SE sounded almost identical… but the ARC was ever so slightly better… more musical.
So, over the last couple years I have done small upgrades to my analog end, tone arm, sub chassis, Phonostage to Reference 3SE. Each improved my analog end… but still they are on the same plain. This basically raised my turntable to the level of performance to the Linn Klimax… which is really very amazing.
As a friend recently told me… “well, it depends on the recording… but, digit frequently sounds better.“ what it really means in terms of listening, is I choose what I want to listen to… which format is not relevant… a wonderful change from the past disappointing digital performance.
That is an extremely abbreviated version of my quest.