Getting into the music

@OP Conversely, as a musician and recordist, I have to turn off the engineering and production side of my brain rather than the audiophile side.

I find it helpful to listen to the radio on an average sounding system - with less information, it's easier to focus just on the writer/composer's intentions.

I think we all go through what the OP described.  In my case I retired 2 weeks ago and my first task was to straighten out my listening room(s), which meant organizing a lot of physical media.  In the course of doing so I encounter many long unplayed recordings and I’ve been listening uncritically from an audio standpoint and having a great time.  I recommend the OP go wading into his vast collection and just play whatever grabs his fancy

Been in this hobby for about 50 years.  IME if you put a well balanced audio system together and use quality sources both digital and analogue, you can enjoy the music. The key is balance.  A mid priced system that has components of similar cost and ability will sound better than a system that has one very expensive component which will reveal the flaws of the cheaper components.  

I feel your pain. Since retiring I have chased "the sound" and finally it hit me. I was wasting too much time in the critical listening arena and not enjoying the music. Then one day, on a whim, I tried out an old pair of Klipsch Chorus ll speakers. I hooked them up to my Luxman L-509Z and played the digital file Hotel California from the Eagles’ When Hell Freezes Over album through my Aurender A20. When Don Henley hit the bass drum and I thought he was in the room with me I realized I was done. No more chasing the ultimate sound. I spent untold hours listening to amps, preamps, speakers, DACs, cables, etc. I found my happy place. I had half a million dollars of gear running through my house over the past two-three years, driving my wife nuts. Only thing left is to do some room tweaks and I am done. Or am I? The plot is always moist...

All I do now is swap out the Klipsch with an amazing sounding set of Harbeth SHL5s. The wife helps with that.

As I age, I always remember I wanted to be a musician and nothing blocks me from appreciate a great music even if it does not sound very well like garage rock.

I now feel necessity to purchase instruments and electronics to practice, create and mix. So moving to more fair and honest industry of the pro-audio