Am I Getting Soft Here?

As once was said in song. “Love the one your with” Enjoy, that’s what it’s all about!

OP, not sure if you were even asking a question that requires a response.  Sounds like you've reached a point of satisfying equilibrium.  Just enjoy it as long as you can, explore new music, share it with friends.

Miller Carbon you certainly are knowledgeable and know what you are talking about.  I will have to go to a local dealer and listen to a tube amp.  Wish was able to spend the money this group spends.  My problem is I have a gate keeper who keeps me in check.  I must say if I spent the money to upgrade I would feel guilty of being self centered and selfish.

There’s something partibularly satisfying about making the "right" decisions that have stood the test of time. Each time we purchase something new, we also have to face the reality that it could have been a poor decision. Over time those decisions are vailidated and our anxiety level decrease incrementally to the point where, in the OPs case, we are totally relaxed with the decision(s).

After retirement, my service tech of 25 years and I spend one day a week trying to prevent disfunctional old audio gear from going into the dumpster. The owners of the gear have very common attributes -- a strong emotional attachment to (generally, mid-fi) gear, and a satisfaction level that’s off the charts. I’m not going to be the guy that goes around bursting bubbles, and "educate" them that their fretwood grille Pioneer speakers are covered up, or the musicality of their Realistic receiver is at 2.7 on the 10 scale. Or, the Sony CD changer’s built-in DAC is generations behind in technology, or their amp's attached power cord is inadequate for a 2-sliced toaster -- much less a serious piece of audio gear, or their idle-wheeled, rim drive Garrard is antiquated. Seeing these guys and gals tear up when lights come back on and music starts playing through their prized possessions makes my day as well.

Thanks for the post. As much as I like the smell of burning hot rebuttals in the morning (they pair well with coffee), this was refreshing.

All the best,

An old audio dude in Missouri.

@larry5729 I think the group is very diverse. I have a gate keeper too and the only way I can upgrade is if I sell my old gear. I regularly have to defend myself like "I sold this for $600, please don’t nag me for buying a used turntable for $610".

I still remember talking to a sales guy in the city’s top hifi store on Boylston Street back in Boston, and that I asked:
"who buys 4000 dollar speakers?"
He said: "You".
I replied: "I just bought 400 dollar speakers and it’s the most money I spent on stereo, or more than all the money I spent, combined.
"Not today. You will buy this in 20 years for sure, you will keep upgrading"

That was 25 years ago. and he was right about the upgrades. I took a break from audio until my kids grew up, and now I am back to upgrading and tweaking again.
I am far from buying $4000 speakers (at today’s prices probably $8000) but accomplishing a lot with used gear.
There are high spenders who sell their equipment at steep discounts when they upgrade that lets my strict-budget type experience the next step up in sound quality