Do you spend more time analyzing the sound of your system, worrying it could be better?

Nope. I absolutely know my system *could* sound better - they always can, but in my case, for far more money than it would be worth. I'm never aware of any system deficiencies when I listen, so hey, I'm done and happy.

The only thing that makes me unhappy is when I play music that I enjoy, but it's only available on a recording that fell victim to the loudness wars era. Those I listen to in the car...

It sounds good to my ears in all ways. Who needs a spec sheet written on it? Be happy!

I like to experiment. What that ends up meaning is that I heard unbelievably good music in my system. OTOH, while I was testing a new integrated amp that I built, oscillation occurred in the left channel. Crap, um yah, not the best sound that I can have. In the end, it is worth it to me to enjoy music in new ways than before even at the risk of not getting it right the next time around.

 Now while this runs true for electronics, speakers are usually kept for years before I decide to change out.

 To answer the question wondering 'what if'? Why yes, yes I do.

No.  Too busy enjoying all the unique and sonically intriguing  music. 

I am as excited when I get a new interconnect as when I get a new vinyl.

Appreciating gears and sonics is the nature of this hobby. No one can claim otherwise while discussing on "audio"gon😀

That doesn't mean music is less important. It is the blood of this hobby.