Has it all been worth it?

Don't regret a moment of it or a dollar of it, although many of both were "wasted" as viewed in 20/20 hindsight. For many of us there have always been limitations and side constraints. Who has the time and money to build a perfect listening room with perfectly matched components before retirement age -- if then? The ideal  is not the goal, but simply the standard of reference. The goal is simply improvement. At all times I ask what is the current weak link, and focus on that  -- until something breaks, or some revolutionary product appears, and then the focus goes elsewhere. A journey, not a destination. A process, not a product.   

As Lilith said on Cheers when reading the will: "that damn bar!"

This darn forum!

For me, first and foremost, it's always been about the simple joy of listening to music.  Broadening my tastes over the decades, listening to what was the 'thang' of that era....symphonies, live concerts, rock as it's rolling along, oddities and audities, dipping ears and mind repeatedly into the seas of sounds and songs.

Not always with SOTA; 'ell, it's been a stretch at times to acquire that 'tad better than adequate' with only the regret of letting some things slip from my hands.

Became a bit of a gearhead when I opted to 'give it a go' to emulate and revise an old legend with a nil budget with reasonable success at it.
That in itself gives me significant satisfaction, if only for my own sake and the time spent in the pursuit.  That I may have inspired others to take up the tools to follow their muse and make the attempt to DIY a Walsh, a ribbon, an amt made by their own hands and efforts has been a boost and a challenge to carry on....

Experienced at various means of manufacture and the materials involved, some talent at 'making it work' beyond mere noise, and gumption enough to ignore a lack of the sheer mountain of 'details' cited in the glowing reviews of Object X vs. my crude ("...not ready for Prime Time....") 'retro-punk' drivers that still cause a pause.

...and have to be tested with music, yet again, at the end of the day...or night, in my case... ;)

I've found Mine.
If you haven't found yours yet.....the rabbit will always outrun you.
Your budget. or lack of, will always never quite be 'enough' even when considered cost no object....

It's reproduction.  It's not R/T.  There will Always be 'that' which will itch....

If it's not fun...Why? 🤷‍♂️

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.