It’s just not the finish, but a lap.
I’ve enjoyed music on all sorts of equipment. I know music lovers who tear up listening to music on their phones. I owned a NAIT3 for over 20 years and viewed it through that time as the massive luxury it is to many many people. I view myself incredibly lucky to own my current system. That is how I would look at it.
I get the equipment side, I really do, but also I think you should not worry. I realise that might be equivalent to recommending someone sprouts wings, but honestly, there ought to be other worries above this one IMO.
I ask rhetorically, as it is categorically none of my business, what was spending money on upgrades really doing for you?
If upgrading has brought you joy and happiness, with a mild caveat that retail therapy is probably not the best! And if you can afford it, why stop upgrading? I have a challenging room too, but doesn’t stop me hearing improvements when I’ve made them.
I do try, fairly hard, to be constructive on here. I hope this is helpful. I’m genuinely sorry if it is in any way objectionable, particularly given the tone of your OP, it sounds like genuine discomfort which I have no wish to belittle.
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I have it bad this year - I had a stable system for a decade and after changing speakers I have the disease bad….
There is nothing to which to adjust unless you used not to listen to music?
Anyway, I’m not sure there is ever a need to upgrade, though desire to upgrade is common. That desire is often quashed by a good phase of upgrading, whether that involves a single item or a whole system, all at once or over a period of time. Whether and how soon it later recurs depends on the individual, and can be spur of the moment or it can start as an itch and grow to the point of demanding action, so having no desire at any one point in time is no guarantee for the future.
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Just enjoy music. Pity you do not have physical media, could be less itching for system upgrade as Vinyl/CD a toy itself. Having only streaming can understand you 
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The best system upgrade is more records!
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I have Naim CD5Si and a Rega P9 as well. Very rarely do I listen to Vinyl. I have a Rega Exact and given how infrequently I listen to LP, the phono stage of my SN3 is fine. My listening frequency order is :
Streaming
CD
LP
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just more emotionally stable 
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In former years I would agree. However it is now very difficult for me to get records in/out of the sleeve and jacket. We have about 2500. Streaming comes first b/c of ease, followed by CD. Records sadly are a distant third.
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More recordings, perhaps, as physical format is irrelevant (other than storage). But of course you have to find music you like - and then you need time to listen to it all!
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Physical format isn’t irrelevant to me. My analog front end is vastly better than digital, and – for whatever reason – I get more engaged in the music with records than I ever do with digital streaming. 
I know others that feel the same way.
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I used to get more engaged with records. However disability makes that much harder. So where does that leave one?
Understand. That’s too bad, and I sympathize. That wouldn’t leave me in a happy place. I have about 5000 LPs. I guess streaming is your best bet.
Nor to me, though my experience is different from yours. But I was expanding on your suggestion that the best upgrade would be more records, which I assumed really meant more music that the person enjoys - hence physical format would be whatever best suits the individual, and could be any format.
Getting the LP on to the TT and operating the TT is not the issue currently. Getting it in and out of the sleeve and cardboard jacket is.
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My comment about it was half tongue-in-check. Maybe it’s a language barrier thing between our opposing sides of the pond and I should have made that obvious.
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I see, and I cannot suggest a reasonable solution around that.
One of the reasons I chose the SN3 and CD5Si beyond the better SQ of the SN3, were their buttons and UI were easy to see. I can operate thE NDX2 from my iPhone or iPad. I keep the NDX2 display turned off. In days gone by, switches and knobs, with clicks, were the prevailing UI, which made things much easier.
I have an NDX2 and also leave the display off. I use Roon, so I control everything from the Roon controller app my 12.9" iPad Pro or my 13.6" Macbook Air. I really don’t care much for Naim’s iPhone app. I don’t like using my iPhone as a remote for anything.