Can an “audiophile” ever be satisfied with a system?

I answered my own question.
It is distracting and misleading to listen to a lot of old, so so LPs.
But when I put on those relatively few good recordings THEN I HEAR THE FULL POTENTIAL. And I do have quite a few of those.
The ones I really like, I play twice or more. BUT, I still hesitate to spend $600+ on three records from Better-Records thinking of my $15 good sounding ones. I have had about 50% luck with 180 gram reissues. I did try 2 Hot Stampers and was not impressed enough to keep them. One, a Super Hot for $99, I could not listen to side 2! Sure, a lot of it depends on liking the music.
The other bottom line is “good enough is good enough”.
But in upgrading there is a real effort to upgrade the sound. It is not merely “shopaholic”. I always think that I love the sound until I do even a small upgrade. With Covid I am listening to my system much more than ever. And because we are now not traveling, I am more inclined to buy.I do listen to digital when I watch Amazon and Netflix at night.
Then it is great but intellectual. But the TT rig is emotional.
“Wow, it sounds great” compared to “wow, I am speechless”.

Dittos to millercarbon. And others. Satisfaction isn't the goal for some of us. If I'm satisfied with the sound I might say to myself "fascinating," and then try the next interesting idea that comes along and that I can afford to implement. I still enjoy music quite a bit even when my system is configured in ways I'm not satisfied with, so the musical enjoyment remains consistent. 

“Can an “audiophile” ever be satisfied with a system?“

Absolutely! Until they’re not.

The Forum has been a real eye opener to many issues around my system and hobby. I never thought a I would not miss my SET before I moved to Atma-Sphere. And now I have a global view on my LP content.
For years, I winnowed down my large CD collection to about 100 that I always enjoy. I have them in three folders next to my office headphone system and love to listen when I am doing biz. I do listen to several over and over.
I've only fairly recently gotten serious about vinyl. I actually have already started sorting out the best LPs. It looks like I will do the same as my CDs with my hundreds of LPs.
Like I have said, when it comes to being satisfied with my system it is really all about 1. Content 2. Content and 3. Content.
Content for contentment!

I’ve realized for me it’s not really about being satisfied, as the urge to “try something new”

recently, I’ve learned cartridge swaps can accomplish that too.  I’ve been playing with some more budget carts like a retipped dl-103 and a sumiko blue point, and even if they aren’t as “good” as what they replaced, there’s enough different and interesting that it has scratched that certain itch to try something new.