Does it ever end?

This will sound silly and counter intuitive, but I’d suggest you get a small, inexpensive rig to swap out once in a while. With no expectation of being able to hear an ant fart, you’ll be able to go from an anal audiophile to just a dude listening to a few tunes. 

It’s worked for me.

I dont think throwing more money nessasarily leads to better sound. This is one of the biggest fallacies in the audio hobby. "If it cost more it must be better" is simply not true. 

Getting an understanding of what actually makes your system sound better would be better time spent than searching for the next expensive upgrade. In fact, many times the more expensive product can lead to disappointment.

Expensive cables are just one example. A speaker cable can't ADD anything to the sound. Not possible. It can only detract. Once understood that  resistance, capacitance, inductance are the important factors then an intelligent decission can be made to fit the requirement. This has nothing to do with spending more money on some exotic cable made from space age unobtainium. However, there is an entire industry built on these beliefs that expensive gear sounds better.

While I do agree that the most expensive component isn't always the best, there are times when you get what you pay for. Sometimes a "giant killer" is just not all that. You can only polish a turd to a certain degree at which point it's often just a shiny turd.

While I do agree that the most expensive component isn't always the best, there are times when you get what you pay for. Sometimes a "giant killer" is just not all that. You can only polish a turd to a certain degree at which point it's often just a shiny turd.

And sometimes the "giant killer" is all that.

Dont you hate buying the expensive one and coming to the realization that it's "the turd" and has been wrapped in a fancy package?

How many so called 'upgrades' are really just an expensive sideways move that didn't really render improvement and sometimes were disappointing? 

To the OP. I have had so many clients feeling as you do. You are listening to the equipment, and you are concentrating on audiophile stuff. You are not alone with this. Having a good/great system (the speakers / room/ sound preferences start here). Our recorded music has several things going on. The music playing; the musicianship (instrument playing/singing) of your favorite artists. The musical composition...the piece/work of the music(song). All of the engineering/ mastering/ compression/equalization (and much more). From the microphones, down the recording chain.....the purity and reality, sound wise, has been lost (compromised), imo. So, what "IS A GIVEN". Our musicians, and the "works"...what they created, what they performed. An audio system, for me, needs to connect me, to these two characteristics, first and foremost. As most audiophiles concentrate on where the musicians are placed on a stage, the acoustics of that stage (spatiality) and the tone of the instruments (remember, these are recordings), I listen, first and foremost, to the musicianship, and the composition. "WHAT" are they doing up on this stage, in front of us. This is the joy for me. I repeated it, because it is important. Most, if not all musicians, listen this way. Try it, you’ll like it. My best, MrD.