The argument against upgrading

You point is valid if you are making a major improvement.   In this hobby there are a lot of lateral moves...  You see it everyday in these threads.    

After many years in this game and many lateral moves along the way I have learned the importance of making a substantial upgrade.   If it doesn't "wow" you at first play it probably wasnt a good outlay of cash.   

If i'm not saying holy $#/t  after I hit play or drop the needle then it's not staying in my system.  That's why home demo or a return window is so important.     

If your system is currently well matched, then, I believe any extensive upgrade should start at the speakers.  For example, are you looking for more bass, extensive sound stage, more detail, Bigger sound, more db,  bookshelf speakers to tower speakers, subwoofer, etc....   So, once you decide about your speakers, then, any upgrade after that will be driven by matching the speakers.  If you are not planning to upgrade your speakers, then, any upgrade that is made should be to match better with your current speakers and provide them with the best possible signal to shine at their best.  Of course, any upgrade, besides speakers, planned with your current well matched system will be much smaller incrementally.  I start from my ears and go backwards...  So for upgrades, speakers first, amp(s) next, then preamp, then, sources - DAC, Streamer, turntable.   All in that order of upgrade.  You can also look at the cables upgrade in the same order.  

I learned my lesson a few years ago.   I had a speaker i really liked , PSB Platinum M2.   A great speaker, actually the last of PSB speakers made in Canada.  

For some reason I felt the need to upgrade.  I replaced them with Revel M106, a very good speaker but I made the mistake of selling the PSB first.   Never again.   I missed those PSB big time.   I eventually sold the 106 after a year or two.  They didnt stay very long.  

I've discussed the point but with a different angle.  IMHO the problem comes from confusing "different" from "better."  It's also true we get bored, so "different" may be "less boring." 

In particular, authors who claim they are hearing things in their music they never heard before are often seduced by signfiicantly different frequency reponse of speakers.  Of COURSE they are hearing things differently.  Is it "better?" 

While it's good to keep this in mind I also think it's good to be true to yourself.  If you find yourself getting bored, maybe budget appropriately.  Instead of looking for 1 set of megabuck speakers, look for 2 or  3  you can rotate in. You may be happier.