Has it all been worth it?

You should not have regrets about your journey.  We are of the same generation, we have experienced vast technological change from the 60’s to now,  We have faced the same challenges as we matured and we have made mistakes.  However, I have an opposite view of my journey.  I have found journey a rewarding process.  I am lucky to be in the NYC suburbs where there are endless opportunities to attend live musical performances, in both hall and intimate venues.  I have developed my perception of how reproduced music should sound.  On my journey, I have always set a goal for the next improvement, and then auditioned new equipment with that goal in mind.  This goal/reward method is the simple psychology of gratification.  Using this process has always left me satisfied with the choices I have made and I have not changed my system often.  
  To me, music is not merely about sounds. Music gives rise to emotional response that allows a change of the state of the body and mind so as to create a state of well-being. The system is only the vehicle for reproduction.   The composition and performance is the vehicle for my response.  
  The enjoyment of music, an addictive behavior in itself, where the pleasurable experience is activated by the same biochemical mechanisms as any other addictive pleasurable behavior, can be hindered  by striving or wanting too much from the system, where one loses sight of the ends (musical appreciation) to focus on the means (system accuracy).  You stated "am I missing out by not owning”. Others in this thread have used the acronym FOMO.  I have not been subject to FOMO.  My recommendation is to not worry about the next best thing.  Focus on appreciating the musical composition and performance for that will provide the “ends” we all seek.  Seek satisfaction from the “ends” and don’t worry about the “means”. 

Definitely worth it.  My equipment has changed as my budget has changed.  Like you after 50 years my current setup is my best yet.  It’s a great hobby and I’ve enjoyed my musical journey.  

Glad to hear of your health recovery, as that is THE most important thing we all sometimes take for granted. 

It's a great feeling to have, when listening to music, that very moment when you think something sounds the best it ever has. After all of the money and time, I'd say yes it was absolutely worth it! 

There has always been a tug of war between wants and available funds. The experience has been the gold all along...

While I have enjoyed the voyage immensely, I have reached a plateau where the quest is over.  My current system is good enough to carry me through to the end, and new enough that it should easily last however long that is. 

I really love the system I’ve built over the years. But if I were to do it all over again, I would seriously consider not going down the rabbit hole. A vintage Sansui G9000 and a pair of JBL L112s would get me 80% of the way there without having to spend the time and money that goes into continuous refinement.