Do you spend more time analyzing the sound of your system, worrying it could be better?

I am in the same situation than you... And i am truthful...

But with a bit of advance compared to many people OVER upgrading gear alternatives possiblities compared to acoustic ...

It is called acoustic method... So powerful that even if an upgrade of gear is possible and it is always possible, in my case i even know what piece of gear to buy but i dont give a damn , guess why?

Acoustic cues are mutiples, and together they constitute an INTEGRAL SET so intricate acoustically that almost no SINGLE piece of gear would have been enough to improve my system on ALL counts WITHOUT acoustic method...

In my case upgrading all my system will cost me at least 10,000 bucks, perhaps 15,ooo i cannot be sure here... My actual system cost me 500 bucks.. 😊 I listen music now , sound is no more a frustration, and it is enough NOW because i have it... Thanks to Helhmoltz not to the "upgrade" of one piece of gear...When a system is relatively good at some point in our journey, we must look for acoustic, not for an "upgrade" of a single piece of gear alone...It will be deceptive to do so most of the times......

I call what i have achieve with acoustic method and a low cost system : a minimal acoustic threshold of satisfaction...It exist objectively but vary a bit from one individual and system to another one...

But when a piano fill the room with his bass note in 3D it is enough to enjoy music without frustration and without lying to ourself, even if there exist for sure better possible acoustic state or experience...

Ratio S.Q. /price is a tag also in our journey, willing it or not....It is here that acoustic method can optimize ANY system to his true potential...Most of the times it is enough...it was for me...

Nothing is more fun than tuning your room save listening music at higher quality level each week during this long process... 😁😊

I suspect a lot of people who answered no aren’t being truthful and have the constant desire to wish to upgrade. I am currently in a good place, but I know that to improve my current set up I would need to ascend to a whole new price area that I am just not willing to enter

@mahler123  I suspect you're correct. And as hilde45 mentioned, this is a hobby, keeping this in mind will keep your mind in order. Keeping your mind in order means being mindful this is a hobby and/or a process to be enjoyed for it's own sake or values, in other words a learning process which is a good thing.

The more I think about the continuing unhappiness I see in the pursuit of highest fidelity the more I think this has much to do with the extreme material nature of the hobby. When expected return on investment/audio purchase not met unhappiness sets in, relatively high expense of high end audio brings expected high level benefits.

I suspect many of us go into hobby with high expectations of fidelity we're going to achieve, when not attained, only avenue seemingly open to us is ever more expenditures, not a good place to be for many.

I suspect realistic goals for those entering audiophile hobby would make for much less angst. How to do this, I have no idea, far too many human variables make this impossible task. I presume most get into hobby after hearing a very nice audio system, or they enjoy live music and want to replicate that at home. This pursuit is not easy and goals not easily achieved. My take is don't even start, try to be happy with what you have, or enjoy the pursuit. While the early years were difficult for me, I did learn to enjoy the pursuit, contentedness with a relatively high level of audio fidelity has been the result.

For me, it begins and ends with music. I've always enjoyed quality sound because I love the beautiful, rich tones of instruments, voices, and that intangible magic. Some people just like to hear their favorite songs, some people like to savor it to very deep levels. It's why I invested in the best gear I could afford. If I had more extra money I'd quite probably upgrade but I don't so I love what I own.

Now, there's nothing wrong with being a tinkerer, gearhead, tweaker, etc. As others have stated, you should be enjoying what you do, whatever it is. If you are worrying, stressing, or unhappy you need to rethink things.

@sns

The more I think about the continuing unhappiness I see in the pursuit of highest fidelity the more I think this has much to do with the extreme material nature of the hobby.

I like the way you put that. The further question is, why is one oriented around the "material"? (Here’s where a Marxian explanation would veer toward a fundamentally materialistic basis of reality and the lives within it. Some psychologists might chase it back to our fundamental rootedness in the body.)

We can see in @mahgister an approach that is joyful in its adjustments and experiments without being dragged into a materialistic -- consumeristic -- quest. He is very concerned with the materials involved in acoustics, of course, but they are instruments to create events and experiences. (In my humble opinion, even a small adjustment by him in the devices embedded in his embedding would be another lever worth pressing, but he prefers to stick with his $500 system. Whatever.)

Adjusting my system is like whittling. It’s fun to do. It’s part of the hobby. And just as with cooking, I like to rotate changes through for the same reason I like to listen to different music or watch different movies.

In other words, the challenge of upgrade-itis isn’t about material after all; it’s about a dogmatic and myopic idea -- that "perfection" is singular and final. If perfection is about plurality and change, the "disease" of audiophiles goes right away, with the hobby left intact.

I have now reached the age where upgrading components leads to minimum sound satisfaction. In other words my ears  don't always hear much improvement in sound quality so I am not getting value for money and there are always other avenues for my cash.