This kills me. Every time. 
Ive ripped 10,000s of my own tracks from CDs to 320k MP3 and FLAC over the last 20 years. Ive acquired many hires files, as well, which are in the 24bit/192khz range. I obsessively test and re-test all versions of an individual recording I can find, focusing on what’s important to my tastes.
I started this process in the year 2000 when I bought a new Nakamichi CD70z + Nak speaker set + custom built Alumapro competition grade subs for my truck. Every new CD was a big deal, and became a ritual where I would only buy new CDs on weekends or days off so I could drive around in my truck for hours, listening and re-listening to every track. Over time I moved to burned CDs, which often sounded like thin, weak garbage because of the compressed files used, and I immediately heard the difference between compressed rips and uncompressed original music.
So I built a 1U rack chassis into an MP3 player, bought a power inverter, and stuffed that 1U in the extended cab. Added a small LCD screen, and pre-configured the windows2k box to autoload Foobar2000 on start, which loaded playlists that I did not have to mess with much while driving. Wired it into the CD70z’s RCA ins, which were hidden on the back of the unit, by running cables through my dash hahaha! Played MP3, WAV, and FLAC on that 1U until I sold my truck and… my Nakamichi.
(had to share that story lol)
As time passed and I acquired better audio gear, I found myself going through the same playlists(mostly electronic, some grunge, some rap & hiphop, some classical) over and over, to listen to fine details of the music, and I was able to A/B/C/etc test different file formats, recordings, playback devices, etc. I marched through plastic, highly tuned, low quality stuff, and then eventually found my way to “neutral” sound and true hifi / hifi DACs, and then I began to hear REAL TRASH RECORDINGS along with very good recordings. =P
My wife and I spend hours and hours playing back her favorite classic records on our marantz hifi, then playing back “Tidal Masters” of the same albums, and then playing back regular lossless/CD versions of the same, and I CONSTANTLY have to intervene.
I dont want my wife to think any less of our hifi, and when I hear her playing like old Bob Dylan or Neil Young recordings that sound like absolute garbage, I go on a mission to find better recordings encoded in better formats. It is essential for me to do this - every single time - because I specc’ed out the hifi and it is not only the hifi’s reputation on the line, but my own.
I justified all the components in the hifi including the Furman IT reference 15i, so I had damn well better find the best recordings/formats.