Maybe critical listening skills are bad?

"Truth is not popular."

Way too true, and that in itself is even less so. Anything that malleable in the day to day light of day in the HO of any given scenario can create a memory of commonality fractured by view and expression given of an impression.

Reality in itself seems to have a slippery substance, right down to the quantum level...one can only hope ’this is where the Edge IS!"

But I’m beginning to doubt that as well.
Does that change how I listen and judge what I perceive from any given arrangement of items playing what may or not be sounds in a pattern I’m not personally familiar with?

Well, Maybe.
Is it engaging, skillful, can you dance to it? Does the gear make it sound like looking at a fishbowl or on the edge of a stage?

You can go with this....

...or you can get on with that.

Me?
I’m going to look @ moon red of bent light.

Dress warm.

I have expressed this before, so forgive the redundancy. I am a Cognitive Psychologist and spent most of my professional life (now retired) measuring people's perceptions of products and correlating those perceptions with product design features to help designers and engineers improve the experience of their products.

It is important to consider that there are two different types of perception. One is based upon the a physical description of a given product and the other is based upon the emotional response of "liking" the product. Typically, two different types of people are used to obtain each of these perceptual judgements. Physical descriptions (probably what corresponds to critical listening) are typically provided by trained experts with proven sensory skills. "Liking" is provided by the perceptual judgements of untrained consumers who are the target audience for the product. The interesting finding in such research is that not all physical qualities to which experts may be attuned correlate with liking. In the end, product developers need only attend on those physical qualities that are associated with what the target audience likes. 

Now, sitting at home the target audience is a sample of one, you. So, the first question is, do you like it? Secondly, it is probably helpful to know why you like it if you want buy things that improve liking in the future. For that you need to know what physical qualities are unique to that experience. You, the listener, might or might not have the perceptual skills to do that. Either way, the first question is, do you like it?

Maybe it’s just me,  but the longer I try to AB things, the things start to sound the same. Sure, some equipment sounds night and day different, but when the equipment sounds close from the start, it really blends after a few back and forths, I can no longer hear the differences.

The better informed a decision is the better the decision.

The interesting finding in such research is that not all physical qualities to which experts may be attuned correlate with liking. In the end, product developers need only attend on those physical qualities that are associated with what the target audience likes. 

Oh, absolutely.  What audiophiles often don't understand is that companies like Bose are _very_ much driven by cognitive science.  The depth of research they do into creating products which are liked, and therefore have financial value in the marketplace is breathtaking.  Absolute perfection of an audio signal is irrelevant.  Engineering metrics only matter so long as they are correlated to being "liked."  Their success in the marketplace speaks for itself.