Monitors

@bumpy48

I don’t think there’s any doubt that this can occur!

However, as no two people hear the same or have the exact same tastes, the point at which any given system crosses over from "highly resolving" to "fatiguing" is subjective. 

Reviewers (and forum members) often address this, whether they be discussing sources, amps or speakers but there is no substitute for direct experience for developing a sense of where you fall on the spectrum. One reason to not buy anything you cannot demo in your room with an option to return it!

@Steakster

I use the term 'improvements' to convey to the reader that I have not just been box swapping, but have been moving up the food chain in terms of cost

@bumpy48 

If you have valve amps and especially a valve DAC, I'm confused by your concerns about fatigue. 

"If you have valve amps and especially a valve DAC, I’m confused by your concerns about fatigue."

Me too

One complication is my tinnitus which is normally very quiet but triggered by any harsh system.

More often my listener fatgue is accompanied by this tinnitus and the whole experience makes me just want to turn it off.  Not good.