The argument against upgrading

I agree 100%  @vvvvvv6 

At this point for us - any upgrades are for visual improvements only.  So, as long as new stuff is in the same ballpark as the old stuff sound wise - but smaller and better looking, it is an "upgrade".  

This is an excellent question hard to answer. With the right speaker upgrade you can make big games. I think electronics tend to be more incremental and a greater risk of making a sideways move for more money. I know I’m considering a new DAC, I think there’s an opportunity for improvement, but I really love the way my system sounds now. When I listen to the music I’ll like the music and I’m not thinking about what could sound better. So, will an upgrade really be an upgrade and even if it is is it worth the cost?
 

It’s easier if you can identify an obvious  flaw in your system, harder when just trying to improve what Already sounds really good.

With respect to upgrades in general - and any new DACs in particular, here's what stopped me completely from even thinking about it:

Me: Should I upgrade from Wiim Ultra to HiFi Rose RS151?

Chat GPT: With your McIntosh MA252 and Focal Kanta 2 setup, the audible difference between the WiiM Ultra and HiFi Rose RS151 is minimal to nonexistent. The RS151 is a luxury streamer with advanced features and premium build, but in terms of sound quality, both deliver transparent playback that your system will render nearly identically.

I understand what the OP is getting at.  However, how does anyone measure, quantify, discern, explain, understand, why any individual audiophile has developed a need/desire/urge (perceived or not) to upgrade his/her audio system?  It really doesn’t matter what you upgrade in your audio system or why, it’s strictly an individual desire/need/feeling, etc.  Who can explain this?  For instance, I have an audiophile friend who still uses his old 1980’s Klipschorn speakers and an old tube amp from the same era, and he has absolutely no desire to change/upgrade anything (his system sounds incredible).  I also have an audiophile friend who is just the opposite, and likes to upgrade/change frequently just because he gets a thrill out of simply trying something new.  Happy listening.                  

I don't really compare one component to another. I compare what I'm hearing to an idealized mental representation of what I want to hear. If it gets me closer to that ideal, I keep it. If not, I keep looking. When I get to a point that everything I have in my system reaches that standard, I'll stop looking and just enjoy it. 

Different is only better if it exceeds that standard. But the bar is high.