Warming up digital in my setup

Glare - that's a great way to describe what I'm hearing.  I'd like something that rounds off the edges :)  - even if it's an artifact.  I know this is all a bit personal choice, but I really couldn't tell a difference between sub 1k DAC (SMSL, Topping, Khadas).  In fact, the Khadas ToneBoard (v1) was the best sounding IMO.  Seems I might need to investigate $1.5k+ DACs?

USB cable is nothing special -- 15ft run - coming out from my iphone.  

Re: Speakers - If I move to anything else, it will be the LS60 and ditch the Hint6 all together.  Parasound & KEF are a great match IMO.  Plus, I really don't want to mess around too much with speakers / amp because I'm finally getting what I want to hear out of my analog setup.  The LS50 are here to stay (for now at least!).

I could be wrong, but I don't think an analog source would be able to compensate for bad speaker placement or bad amp/speaker combination.  If it was a setup/pairing issue i'd also loose the depth and soundstage. 

Border Patrol, Orchid, Denafrips Aries have always been those next level DACs.  That's probably where I need to go.  DAC aside, would cable length, connector type really have that much impact?  

Yep, seems the DAC needs replacing  ....  which is unfortunate.  I'm quite happy with the built in phono stage, but IMO they missed the mark with the DAC; but i digress.  

Seems I have a couple of avenues to try - both dedicated devices - DAC & Streamer.  I don't have access to any of these devices locally; I'm limited to online retailers.  I also don't want to make alot of changes at once.  Likely, the biggest bang for buck here is the DAC, wouldn't you agree?  When I tested < $1k DAC in my system (both headphone & speakers), I was left with how similar they all sounded.  The $140 Toneboard that I use for my bottlehead HF amp was great, and the $900 topping, SMSL or similar didn't offer that much more.  

So, in terms of pricepoint, I'd have to go to the next level which is likely, BorderPatrol, Orchid, Denafrips, Yggdrasil type quality. 

@zlone I'm intrigued by your Pi/Allo setup.  Early on, my first headphone setup used a Pi w/ HiFiBerry Hat.  It worked out really well to stream Spotify -- it was basically set and forget.  I still have a few raspberryPi 3 and 4, so I'll check this out and report back!    

Just wanted to report back that I changed up the streamer.  I received the Digione last night and provisioned an RPI4 w/ volumio.  My first impression - I'm astonished that it made such a difference.  In the few tracks I played to test, the almost unlistenable glare is gone.  It's still a ways from the analog detail and warmth that I'm after, but this was a significant step toward that end.  I can't imagine what an upgraded DAC will bring.  

The best part is that its portable - so I also tried it with my Bottlehead Crack w/ (budget) Toneboard DAC.  Bingo -- at the very least much quieter background (in addition to the Digione, improvements could also be attributed to using SPIDF on DAC instead the dual data/power setup that I had via USB).

Overall, I'm impressed to say the least.  I'm going to let this setup burn-in for a while and really listen to it.  Much appreciate the recommendations!

Next upgrade with be to an Orchid MHDT or Border Patrol DAC