A DAC that can make digital sound analog?

I have always been a vinyl guy, and also had CD players and then DAC's that did the digital chores.  IME digital kept staying clearly inferior due to something just not right in the highs - - until I started using R2R DAC's.  I first built an Audio Note Kits 4.1 LE DAC, and it just had musical soul like my string of CD players had not.  Then I got on the Lampizator train, and have not looked back.  I found the Big 7 to be very competitive with my vinyl rig.  I would strongly suggest looking for a deal on a good used Lampi for something that can pair successfully with a vinyl loving system and audio nut.

I bit hard on the vinyl bug for about three years. Had an analog rig that was about 7k all in, and 600+ LPs which were curated in such a way that they are the very best pressings of the music I wanted. Several Mofi One Steps, AP 45 RPMs, original Floyd, Zep, etc... Taking any "vinyl noise" out of the picture, the sound quality - not as a function of stark accuracy, but rather, how into the music I could get. How emotional it felt, how it moved me. It was amazing!

Then I got an Yggdrasil (with updated analog out board) and a very nice CD transport, and some CDs. I get that exact same window into the music, but the media is far less fussy, there's no real setup to deal with, and I can pop in the disc and just hit play, same ritual as vinyl except no sides to flip. 

I will be keeping my vinyl stuff, I just don't use it nearly as much, now. 

I have analog rig but its usage dropped significantly after my Marantz SA-10 was fully broken in late last year.  It's the master tape transfers to DSD (up to 2x, 4x) by 2xHD and others that really impressed me (bought from Native DSD and HDtracks).  Live recordings straight to DSD is also very good by both Blue Coast and Native DSD. 

I built my own digital player using Intel NUC7i5 and use USB to SA-10.  I still play CD and SACD physical medias occasionally. 

The upsampling of Redbook CD to DSD 4x enables more details to be heard.  Despite that, Redbook CD does not sound better than true-analog vinyls.   It's the DSD format that killed my analog rig which costs 4x more than SA-10.

The convenience of selecting albums/artists from smartphone, jumping tracks, the lack or surface noise, no need to change vinyl sides make me just relax while listening.  However, when the sound is too perfect, some of my hard-core vinyl friends don't like it, but that's not a problem for me.

My suggestion is to go into hires if you want the best from digital.

I'll never understand the PS Audio Directstream love.  It sounded distant, soft, and boring in my system.  Too laid back.  Maybe it was just poor synergy but yeeesh.  The touchscreen they use on there makes it look super dated as well, the credit card swiper at wal-mart looks better.

The T+A DAC 8 DSD sounded much, much better in my system, and it retails for $2k less.  It really takes that "digital" sound and throws it out the window, particularly at 512 DSD.  The soundstage is massive and 3D.  It has tremendous body with vocals and bass has great weight.  It has very high resolution without sounding skeletal and uninvolving - and that is a RARE combo in the DAC world.

I’ve used Mytek and Bryston DACs, after upgrading from an Opp 105.  Both are fantastic, with the Bryston being a bit less clinical sounding.  The Mytek have multiple filter options that you can experiment with and are MQA compatible