Is advice from a constant upgrader to be avoided

"Gear shifters"....some are manual, but there's a lot of automatics on the lot...;)

Truth be told, I lack the disposible to run in the SOTA wheel of audiophilia, and have for most of my years past 30ish.  Nor the leisure to spend discerning the details 'twixt A>Z anything, esp. since my hearing has admittedly required the application of 'onboard appliances' to render any profound 'imho' on any object of audio obsession worth your reading about...

I have learned what and how to make the items in my possesion recreate that which I enjoy listening to in the spaces I happen to have them in.

Some may 'snarf' and opin that "You'd be better off with a Dixie cup at the loose end of a string!" or some other not-so-pleasant response.

Note that I will not subject you to listening to it unless you stumble into my presence, or ask to be subjected to it.  I do have a relative amount of regard for your inattention or basic civility.

Basically, it's a hobby pursued to enjoy music in a fashion that's done specifically to do just that, enjoying what's heard when I click the mouse, drop the needle, or engage the laser.

I only have to please myself...sometimes, even be impressed by my efforts to my own perhaps lackluster levels.

I suspect you're doing more or less the same.  Enjoy. 👍, J

This is an interesting question. I am firmly in the not-changing-for-a-very-long time camp but when I think about it that has two main reasons. First I got a family and did other things for many years which meant I did not have as much time nor money to think about hifi upgrades. Now I have some more funds but not enough to upgrade everything over and over. Maybe I would be a real flipper if I had the funds?

I am in the process of planning my next upgrade which I hope will happen within a year or so. I might upgrade two parts of the system. One hard question my wife asked was "if you do this upgrade now for $X, are you then done?". And even though I have upgraded very few things the last years I don't really like to decide now that I will be done. Of course I could live with that for years but if I have the financial means it may be interesting to upgrade something or everything again within the next 5 years or so.

As for who is best to listen to, there is a downside of listening to me or anyone else like me, I have not had that much gear going through my home. I have mostly heard new things at a dealer or at audio shows. I think you will hear more nuances when you have a piece of gear at home and can listen for days or weeks to it. If I were to recommend a dac right now it would be from dacs I heard at dealers or shows or from what I've read. Or, a very, very old dac which I don't think is of much interest for you.

So I do pay attention to what some "flippers" say also. I do add a grain of salt to some things or try to interpret what they say and think about if that thing they did not like as much as their new gear could still suit me. If someone says that their new $10k dac is much better than their old $5k dac I think it is interesting but I still don't have a $10k budget for a dac (right now) and if they say that they have tried three $5k dacs at home and choose the last one it may still be interesting to hear what they liked or did not like with the other dacs.

OP

you ask a terrific question.  My inclination is to agree with your premise.  Otoh, with the demise of bricks and mortar dealers, it's hard to make an intelligent and informed purchase.  And we don't really know how anything sounds unless it has resided in our system for some time, been broken in, and we have had a chance to play a variety of music.  So while some people change gear more frequently than they shower, others are trying to get things right in a challenging hobby.

System/component synergy is also a real consideration when doing "upgrades". Just because a certain piece specs out nicely or gets gushing reviews doesn't mean it's going to sound good in YOUR system. Sometimes, just getting the right combination of gear will get you performance in spades.

One thing that I'll add to my earlier comments is that a lot of the experimentation I've done in my system and the knowledge I've acquired is a direct result of getting to know other enthusiasts and picking their brains and finding some people to mentor me. 

Join a local club if you can and then get to know the members that seem to really know their stuff on an individual level and spend time listening together.  Listen to their systems.  Ask a lot of "how" and "why" questions.  Invite them to listen to your system, and ask for honest feedback.