AMR DP-777, what am I missing ?

There are a lot of people here who love this DAC, I purchased one (used) based on the many glowing reviews, but feel like this DAC falls short.
To be sure it bested (by not a lot) my Wavelength Cosecant (better imaging and bass) but I still prefer my modest analog setup (Rega RP6, Shelter 500).

I am sure my digital front-end is not super tuned: IMac, audirvana, no-name USB cable to DAC. But before I spend more money I would love some advice from the good folks in this forum on how I can make this $5000 retail DAC at least come close to my modest analog setup that cost much less retail without spending too much coin.

Do I need to invest in a music server, or maybe a USB to SPDIF, or better USB cable or all of the above.

Rest of my system.
Coincident Line stage
Coincident Dragon mk2 monoblocks
Verity Parsifal Encore speakers.

I'll be interested in reading some of the replies here.

Your story is not all that unusual, as far as I'm concerned. In fact, I gave up chasing high end digital separates years ago when I rediscovered analog.

I have a nice Marantz CDP that handles my digital needs, and has kept me satisfied digitally for the last 7+ years. I'm sure that digital gets better, but it still doesn't compete with analog, IMHO.

I own the DP 777. The cabling and USB could add a smidgen more detail and decay but you are not going to replace the organic nature of analog. Unless your willing to spend much much more. The AMR sounds good and is real convenient for computer audio or even with a lower priced transport. But for critical listening or to enjoy music the way you have built your system save your money. AMR has just started shipping the boards for the SE update but I am going to save my money and buy LPs. You will probably get as many different opinions as the posts you receive.
I'm having similar issues but slightly different. I purchased a Resolution Audio Cantata here and so far this is my experience. Playing CD's on this device is absolutely glorious and terrific. Digital off the computer, no where close but my digital set up is similar to yours, generic cable etc. so who knows what it is capable of. Oh and my analogue front end which is a Rega P9, terrific as well in a different way but the Cantata CD playback is quite "organic" as well. I'm anxious to optimize the digital playback but not for crazy money. I'd Rather buy some more lps or CD's.
I was afraid that was going to be the answer.

Was considering selling my analog setup to reduce the number of stuff I own, but guess not yet.

Redcarerra, I am considering getting the ifi usb stuff to see if that could help. Mattshipln huge thread has considerable info on making digital sound better.