Ok, I'll try to explain what I mean here...
While I certainly don't have the highest-end system, it's ok and it frequently makes me very happy. I use Roon ROCK on an NUC into a NAD Masters Series M50.2 player/vault connected directly to a NAD Masters Series M32 digital integrated amp. That connects to a pair of CSS Criton 2TD-X towers with upgraded crossovers, which are supplemented by a pair of Taket Live supertweeters and Taket WHDpure "woofer hi-definitioners."
On the analog side, I have a heavily-modified Rega table into a Moon preamp with outboard linear power supply, which goes into a line input on the M32.
Cables are Hapa digital and Audio Art analog.
So...I LOVE the sound I get from well-recorded HD downloads (such as the Nagra 70th Anniversary 2xHD Jazz album and Nuvelle's digital offerings) and when listening to those I have no desire to upgrade any gear whatsoever. But I'm left wanting on many of the non-HD digital recordings I own.
Similarly, UHQR vinyl sounds awesome and inevitably takes me where I want to go, but run-of-the-mill vinyl is often meh.
Is some gear simply too unforgiving with mediocre recordings, and can better gear help me find happiness when the recording isn't great or the digital resolution is lower? Or does better gear inevitably result in dissatisfaction with undistinguished recordings and I would be better off just gradually replacing my entire library with HD music?
The trouble is with mediocre equipment, is you never hear the potential of any recording - good or bad. However with high end equipment, at least you hear the good recordings at their best. You can always pass by the poor recordings.
I see you use the NAD M50.2 and M32 - precisely my setup 3 years ago. I upgraded from M32 to M33, which includes a streamer, Dirac Live and has an even better amp technology.
You seem to have relatively inexpensive speakers, perhaps home built as I see a flat-pack version for a little over £1K. It also seems that you've deemed it advantageous to add a super-tweeter and "woofer hi-definitioners", whatever they are!
By contrast, whereas I have almost identical electronics, I've put far more into my speakers (perhaps too much) with Avantgarde Duo XDs, your speaker investment is small and perhaps rather less than up to the job of matching the potential of your electronics – or the better recordings you play through them!
I hate to criticise vinyl users but I often see a hugely costly playback system (and presumably a costly collection of records) and I wonder how much time is actually spent playing these records. Do most owners listen to streamed music (vastly more choice than even the biggest vinyl collection), or do they get up to put on or change a record every 20 minutes each day? I suspect the former, so I've long since ditched vinyl and more recently effectively ditched CDs although I can still play my stored CDs using the now rarely used M50.2.
I see the point of your question. I think most of your kit qualifies for your "great gear" description, but perhaps I would re-arrange my investment by selling all vinly (hardware and software unless you play it daily and can genuinely believe it sounds better), and significantly upgrade the speakers with ones that don't need super-tweeter or any bass enhancement. Next phase, consider upgrading the M32 for M33 as I did 3 years ago. This is a first-class bit of kit at a genuine bargain price - good enough for Stereophile to award it 3 annual "Best of" awards in one year. If you buy used, both a pair of gutsy speakers and an M33 should be spotted at about half their list prices. Note that NAD has announced the M66 that offers all the M33 does, but better all round, except that it has no power amp - it's a streamer / DAC / pre. This will be my next upgrade if it sounds as good as its spec suggests. Good luck.