Critical listening or a reason to keep tinkering?

I agree with what @geoffkait says...go and find some other systems to create a contrast to your current rig. It could help to ease the "paranoia" :)

I’ve heard some setups that I thought were great..after several upgrades of my own, I go back and listen to some of those setups and some seem fatiguiging, dull even.

I’ve even heard some systems that on paper should sound terrific but did not please me. Sometimes they were what I thought was too technical and bright. Maybe this does sound great to some but didn’t do it for my ears..I came away with an assurance that I like my sound and the upgrades I have made along the way.

So so many factors to consider. Maybe you have a killer setup but your room or placement needs work.

if I think my setup sounds better, it’s not because it is, it’s just because that’s what does it for me.

Agree with bdp24, more music.

As audiophiles, we have an inherent drive (maybe NEED) to analyze, tweak, and pursue. Average just won’t do for most of us. And that’s fine—but it’s preciously easy to get carried away. That’s why it’s smart to have your priorities and expectations set before jumping in. I didn’t have my priorities set. At least not at first. I was on the component-of-the-month merry-go-round for a long time, and as exhilarating as it seemed at the time, in the end it wasn’t very rewarding. And it cost me a LOT. I have no illusions that the rig I have now is the end-all/be-all, but I put it together relatively slowly and intelligently, guided by firm goals and helped by a manufacturer friend of mine, and it has proved its worth over the long haul. It’s lasted by far the longest of any of my systems. 

BTW, I echo the suggestion to buy more music. That always makes me less anxious about audio stuff.