I think some perspective helps. On the DAC side, there was a rather dramatic improvement in sound quality from the introduction of CD through the Introduction of, say, the Levinson 30/31. And, for me, while digital sound has improved, the improvement is smaller than the leap from the introduction of digital music, via the CD, to the release of the 30/31. I'd suggest, based on hearing a 31.5/30.6 vs. a dCS Rossini, that there has been less improvement in terms of sound quality over that timeframe than before. It's rather funny to host a demonstration (well, pre-COVID) and to play something modern, like the Benchmark DAC3 vs an old Meridian 563 or 566 or an older Theta or an older Wadia. Most people say the older DACs sound better - go figure!
Streamers appear to have undergone a similar rapid development that is now slowing. Martin Colloms implied that the Naim ND555 with two 555 power supplies is the finest source he has ever heard. Interesting, then, to juxtapose that with Naim's own R&D head saying there was not a clear winner between the ND555 and its predecessor, the NDS. Less expensive streamers appear to be the beneficiary, as their price/performance ratio appears to be improving as companies work to improve them. On the other hand, the sonic difference between the newer Naim NDX2 and its predecessor, the NDX, is relatively small, which the NDX2 counters by providing more services (amongst other things).
So, to answer your question, I'd say find what you like and stay with it. "Worth" is entirely too subjective and dependent a term for anyone to answer here.
Streamers appear to have undergone a similar rapid development that is now slowing. Martin Colloms implied that the Naim ND555 with two 555 power supplies is the finest source he has ever heard. Interesting, then, to juxtapose that with Naim's own R&D head saying there was not a clear winner between the ND555 and its predecessor, the NDS. Less expensive streamers appear to be the beneficiary, as their price/performance ratio appears to be improving as companies work to improve them. On the other hand, the sonic difference between the newer Naim NDX2 and its predecessor, the NDX, is relatively small, which the NDX2 counters by providing more services (amongst other things).
So, to answer your question, I'd say find what you like and stay with it. "Worth" is entirely too subjective and dependent a term for anyone to answer here.