@kerrybh +1
I’ve been contemplating how to give a thoughtful answer to the thoughtful question posed by the OP. I don’t think I’ll do better than the above but will add my $.02.
I’ve enjoyed every stage of my systems development over the years. As I made one improvement, I found myself desiring to make other improvements - because it was both fun to see (hear) “what if” and musically rewarding. It was also sending me down the proverbial rabbit hole. Upgrade here led to upgrade there.
I have several times concluded I was done, just wanting to sit back and enjoy the music, only to eventually explore another what if.
Where am I at now? Well, I stumbled into the category you are inquiring about with my DAC/preamp and cables. The speakers and amp are certainly nice, but fall well short of TOTL. Each piece was chosen based on a combination of performance, what my room would accommodate, aesthetics (I don’t want to look at gear), budget, and what was available from dealers I know, like and wanted to support.
Based on that criteria, in my room (a notable limitation), I find my speakers give me 95% of what I’ve heard from the best (other than MBL 101 MK IIs - but those didn’t meet the aesthetic requirement). They’re very satisfying. Will I ever upgrade? I can’t say.
On the DAC/preamp and cables? They’ve given me more of everything, allowing the speakers and amp to give their best. And yes, to me it was worth it though I can easily imagine others thinking me quite the fool. But they really were notably better than the gear they replaced (which was already good) and what I heard elsewhere. Better than other TOTL gear? Doubtful, but I had sound reasons for the choices I made.
Is it all worth it? I would never say one way or the other for anyone else other than to say never risk your financial independence over audio gear. Assuming that’s not a concern, I would suggest you step gently and try a piece here and there to see if it brings you the satisfaction you desire. It can be a fun journey, though be forewarned: I’m pretty sure no one actually gets to the final destination.
What’s next for me? Not sure. I still wonder about my amp but substantively improving it would require a big spend - and I’m not sure I’d get that much more anyway. And, I am considering the Taiko extreme and Olympus servers - though that feels like it may add complexity I don’t need. And they are changing things quickly in that space.
So today, I’ll enjoy the music. Hopefully I’ll do the same tomorrow. And then I’ll go AXPONA and I may stumble again.
Best,