The argument against upgrading

First things first.Love of music and musicians should be 90% of your emphasis.Once you have a system that you enjoy your done.Spending your money on music is the prime reason for the hobby after that.Once I realized that my foundational feelings for music were laid down listening to a transistor radio in my bedroom at the age of 8 my pining for better and better gear seemed infantile and juvenile at best.

@newton_john great discussion you've started.  Maybe I'll have a nugget worth sharing.

One thing I haven't heard discussed is the type of music people like.  I think complex orchestral works are maybe the toughest for a system to handle due to all the dynamics and soundstage required to fully reproduce a symphonic piece.  So those that listen mainly to classical, I think probably are more apt to upgrading their systems compared to someone that likes jazz or bubble gum pop music.  The genre does matter.  If your systems goal is to reproduce the nuances of a live orchestra, it's going to be a life long journey.

The other thing I haven't heard discussed is that an upgrade can sometimes reveal flaws in other components.  So what wound up being a single component upgrade becomes a money pit as you realize how you need new cabling etc to refine the sound.  This happened when I demod a T+A Dac200 and realized uh oh, the clarity I'm hearing now reveals that other components need some taming (speaker cables, power cables possibly) and decided no thank you on another rabbit hole.  This is a super important consideration in my opinion.  Sometimes one component change, especially speakers, amp or DAC can throw you down a whole new price tier.

Another thing is that sometimes "better" is not better in all context as maybe some recordings sound more harsh or etched on a better system.  A lesser system can provide some "cushion" to some of the harshness we can hear.  Probably one of the reasons that people choose vinyl or tube amps (not to say there aren't harsh sounding vinyl rigs or tube amps but generally they are "softer") . This isn't to say not to upgrade.  Just remember it may throw you down the rabbit hole of synergy that can mess up your bank account and take you away from listening to the music.

If you really love your system, probably best to keep the speakers and amp you have and try to match components outside of that to tweak it.  Food for thought

Sometimes I have looked back at my upgrades and the incremental improvements made. I don't know that I can say any particular component upgrade "made" the system, but each one did improve sound quality and/or presentation... especially moving up from Audio/Video receivers to a quality integrated amplifier. Then quality separates. Quality speakers are also important and I believe worth the investment, but they are also very personal. I wasted a lot of time trying some recommended speakers that weren't that good in my system. Fortunately I'm done now. Having said all this, my bedroom system is 1/10 the investment yet I enjoy it immensely when I'm in there.

It's been said that the sequence of "knowing" goes something like this:

1) you don't know what you don't know

2) you know what you don't know

3) you know what you know

4) and, you don't know what you know.

I'd like to use the following as an illustration:

We run a part time repair shop with the purpose of keeping good audio gear from winding up in the dumpster.  We commonly see equipment come in that was purchased when the owner was in college, just moved in to their first apartment, or inherited/gifted from deceased family or friend.

In their minds, their gear is still the Holy Grail of audio performance. Some of the gear is, at best, "mediocre" often including model numbers we've become quite familiar with.  Like the number "9", followed by "oh" then "one".

We're in the repair (sometime restoration) business, not the soul crushing business.  Telling a guy that his stuff "wasn't worth the postage to send it over here from Japan", or "those speakers are perfectly fine ... as long as you don't try to play music through them"  is not a good way to make friends.  So, we fix what is broken and take our little Q-Tips and remove 50-years of nicotine stains from the rear the front glass.

The bigger point here is that these are functioning systems that still provide thrilling performance to their owners.  They would immediately turn down an offer to trade even up for a stack of the latest (competent) gear at 3x the value of their gear.  I'm certain that I could "persuade" them in 3-minutes or less just how much music they are leaving in those boxes (errors of omission) or how much "other stuff that shouldn't be there" (errors of commission).  But, why?  Our "upgrades" are usually limited to replacing those (awful) preamp jumpers.  Taking them from "you don't know what you don't know" to "yep, my stuff sounds like #&*#$!!" serves no real purpose.  Yes, we do performance "mods" but only after the customer has indicated they love the form and function of their gear, have a strong emotional attachment to it, but would entertain the concept of it sounding better than it did when it left the factory.

Related to "upgrades" in general, my most positive experiences (as in BLOWN AWAY) have been those concepts that initially pegged the needle on my BS meter, reluctantly auditioned (as in dragged kicking and screaming into the demo room), and discovered to be legit.

@mahler123 

I’ve been listening to the Songs for Groovy Children Hendrix box set this morning. In high school, Band of Gypsys was a favorite of mine. At age 69,  I don’t believe my enjoyment has diminished one iota but how I’m listening, what I’m focusing upon, certainly has. Way back when, it was largely "raw sensation" ; I couldn’t have verbally communicated what exactly was affecting me when I heard these tracks. I felt a power in them that grabbed hold of me emotionally and physically. It was  intoxicating, in a similar way that smoking pot would later become. Listening offered a  pleasant sort of disorientation; a sense of "getting lost in the music".

Now, with many more decades of listening and playing guitar under my belt, I’m focused on what is actually being played and the interaction between the musicians. Do I still feel "intoxicated" ?  Well, yes, but I don’t feel lost or disoriented. I feel intoxicated from being more present, more focused on the "details". Having said that, my system is quite modest, so the degree to which the details are now evident is as much a function of a developed ear and understanding of music as they are a function of improved fidelity. Is it the same as when I was 14? No. Would I trade my current experience for that of the fourteen year old’s? No.