If you have problems with the gear flippers, you can always go to the ignorant for advice. As we all know, lack of experience is a huge advantage. ;)
Don't think for a moment that holding a system for decades is advantageous, except fiscally. In terms of sound quality, it's gentrification. You assure the sound quality is slipping further from SOTA the longer you hold on to your system. If the goal is to not spend money, you have done well. If the goal is to advance your rig and listening experience, you have not done well.
Now, watch, we'll have a diatribe or two from our "thrifty" members who will blab incessantly about how money is fairly disassociated with performance, etc.
I am a System Builder, who loves working with different gear to hear the result, and there is absolutely nothing wrong with that. It is no worse than the person who does DIY equipment and pretends they have vetted it against manufactured products and claims their homemade stuff is superior. It's no worse than the Mediaphile who has a so-so rig, but spends inordinate amounts of money on media.
There are all sorts of perspectives and approaches to this hobby. You don't like the gear flippers? Fine, find someone who anchors to their gear and take their advice. It's not life or death.
mid-fi-crisis, you summarized, "
Is the constant flipper/upgrader always going to say that the gear they used to own was no good and they've now got better? Maybe their constant searching is because their ear is no good or they're addicted to the rush of opening a new box. "
You are overlooking another possiblity, one you may not like. The performance spectrum is much larger than you seem to realize. Show me a gear flipper who is habitually moving backwards in sound quality? You won't find many. They are advancing their systems, and why? Because the spectrum of performance is enormous and it goes quite a ways upward into SOTA. Nothing wrong with their ears at all. They just realize that there is a lot more out there to obtain than the average person realizes and they are committed to it. Most audiophiles want to pretend they are really pushing to get SOTA. No, they are not. They give lip service to it. They don't put in the money, time or energy into it.
Being a reviewer has allowed me to explore parts of the performance spectrum I never would have visited otherwise. I change gear to go deeper into the performance spectrum. So, is there any inherent advantage to listen to someone with less expereince? No, as ignorance is not terribly helpful in this regard. YMMV
Again, we will have all sorts of inexperineced types or chintzy audiophiles arguing that this is all wrong. I do not care about their opinions and have no interest in debating my discussion.
When I wish to learn, I pay less attention to what others say. I build systems, and imo so do those who are actually working to obtain superior sound.
So, pick; get your advice from someone who is largely ignorant of the performance spectrum, or someone with much more expereince. You pick your authority, you get your results. :)