Has it all been worth it?

It has been worth it for me.  Although early in my audiophile journey I did a lot of upgrading, about 40 years ago I assembled a core system that has proven satisfying.  I've had to upgrade parts of it, and particularly I have had to upgrade the digital side of my system, but now even that is quite satisfactory.

I can simply listen and enjoy the music without having to be critical about this or that detail.  I really believe that for my system the biggest shortcomings are in the recordings themselves--I have found few convincingly realistic recordings, but the difference between them and the rest have convinced me that one's reproducing gear can only go so far--you can't make a silk purse from a sow's ear.

But if the acoustics of your room are not good, you either need to address that or focus on headphone listening, which I can enjoy while realizing it misses some of the elements that loudspeakers provide.

@craigvmn 

My older brother thinks I’m out of my mind for having the rig I have.  He’s very happy listening to his music from the 1/4” speakers in his phone. While I do listen the same way from time to time, I truly enjoy listening with my main system a lot more.😃

Heck, this is a fun pastime.  Chez xeno has always had a fun stereo since the earliest iteration: components were sourced from Goodwill, St. Vincent De Paul and other thrift stores...think $15 Heathkit tube integrated and $25 Dynaco speakers.  Lotta evolution, all fun, and now we're enjoying our end game system.  So yea, it was waaaay more than worth it.  I'm truly saddened for anyone who hasn't had similarly enjoyable experiences growing their stereo.

Yup.  I sold hifi in the 80's.  I don't have what is considered a pure audiophile system but it gets the job done better than anything I have ever owned.  I don't have FOMO.  I don't have upgrade-itis. Play on!