Has it all been worth it?

We all go through cycles...  When I get bored of my system, it is usually because of the same old music.  One thing I have done that has been very interesting is look at  stereo equipment reviews online and note the music the reviewer is using to test the piece.   Then, I go to Qobuz and listen to it.   It is usually a super quality high res song.   If I like it, I will pay the $2 and down load the high res version.   In this way, I have found some fantastic music, that still adheres to my taste, and makes my system shine.  I have received comments like, " who is this"; "wow", "great song", "great recording", etc... using this method.   Give it a try, it is a cheap way to change it up. 

Yep!  I’ve been at this for 40 years. My Dad is an audiophile too and I came up being dragged to stereo stores for hours. I was born into it. We go to audio shows and have a great time.

I’m a music listener, not a “gear listener”. I upgrade seldom, but when I do, I usually go big (or as big as I can reasonably afford). A friend of mine once told me “you can really justify just about anything you spend on that stuff because nobody gets more out of it than you do.” I keep trying to convince my wife of this. 😉

I think there is a time when you have to concede that you’ve taken your investment as far as you reasonably can. But the good news is there’s always more music to buy and listen to. Either way, I win.

Only you can answer that as it's a singular perspective that we all have. 

For me, with my small budget, DIY speaker builds and skip rescued tube amp restoration, and repurposed 90s sampler as a DAC, it's been very 'worth it' ! Confirmed in full last year when I was treated to a demo of a £40,000+ system in a local HiFi emporium to discover that my budget vintage system sounds just as impressive. I heard nothing I wanted to own and saw nothing I found as nice to look at. 

Definitely yes. And you don't have to spend too much to have a very good satisfactorily sounding system. There is always something better out there, so what? Your system must be capable of conveying the emotional essence of music, the rest is less important.

Yes it has been worth it. Never second guess yourself as there are others that will do that for you. 
Enjoy the music.