Upgrade Suggestions please

Nice system.  
You have a lot more invested in your analog system.  The turntable alone costs about 4 times the streaming source.

  I have never actually heard an Eversolo product but what I have read from users is mixed.  Can you get a loan of a better streamer and then see what you think?

I can guess you wanna spend but imo there is no upside if you think your analog setup is better. keep your analog setup

I owned a Merason Reuss and it was very musical, but also on the warm side. I replaced it with a Bricasti and it added more life to the system. You might try another DAC to see if it opens things up a bit. Nothing against the Merason at all, it is a great unit, I had it coupled with warmer speakers and it was too much.

I don’t know how good the Eversolo is, there is likely room for improvement, but I would start with the DAC.

@maprik 

In my opinion, the ultimate goal is to be able to enjoy both formats. I go on a weeks long vinyl listening spree and then switch back to digital. It takes me several hours to adapt to a completely different presentation. Both formats have pros and cons. 
 

I would recommend getting your digital to the level where you really like and enjoy it. And then stop comparing it to analog. 

I can tell you what I ended up with after years of experimenting.  I now have a Meitner MA3i DAC and use its in-built streaming card as a Roon endpoint. I also use Qobuz and Tidal Connect options as well as JPLAY. 
What I absolutely love about the Meitner DAC is that it sounds very natural, has great detail delivery without ever being in your face. It upconverts all incoming signal to DSD1024 using Meitner proprietary FPGA. 

Add MA3i to your list if you’re looking for a very high quality digital playback.