Upgrading digital side

Really depends on what specific improvements you’re looking for and what sound characteristics are most important to you, especially for the DAC so I’d suggest sharing what specially you’re looking for to get more helpful/meaningful recommendations here.  With a really good streamer with storage you may find your CD transport being very rarely used, so I’d keep the Jay’s at least initially until you see how that works out.  By most accounts Innuos’ Sense app gets the highest marks for usability to the point that some Roon users ditched it once they had Sense, and I’ve not heard that said about any other streaming app so may be something to consider on the streamer side.  One thing I’d budget for is also upgrading the entire digital chain including the switch, Ethernet cables, etc. as those ancillary pieces can be critical in matching and possibly surpassing the sound quality of a really good CD transport.  Like everything in audio the chain is only as strong as the weakest link and everything matters, and that definitely holds for the digital chain.  Just some thoughts FWIW, and best of luck. 

I would also consider Antipodes on the server/player side, they offer a lot of flexibility in terms of software options, and their hardware and support is excellent. Worth a look.

• Server
• Streamer/endpoint
• DAC

How you stream music makes a difference but, in general, my experience is that your money should go in the opposite order of the list above, with most going to the DAC to achieve the biggest bang for your sonic buck.

As you pointed out, the Grimm MU2 does it all, and very well based on most reports.  You could also consider something like Meitner’s MA3i, which serves as a streamer, DAC, and even a volume control, but you would still need a server to run Roon core and store your files.  At reasonable prices, I have had good luck with Small Green Computer servers, especially when paired with a good streamer, like Sonore’s top model or something like the Innuos Pulsar. Separates work well, and particularly for flexibility but, at your price point and considering your needs, you might find that the Grimm delivers it all. As pointed out by @soix, you could rip your CDs to the server and then sell the Jay’ to increase your budget for the new stuff.  Ripping to a SGC server is a piece of cake.  I still occasionally buy and rip CDs even though I have nothing to directly play them on.

You have a good digital system already; a lot of changes, even more expensive ones, may be a sideways move. I find Primaluna gear to have a sound of its own, and not necessarily super transparent — you may benefit more from system matching than ‘upgrading.’  To use an extreme example just for illustration, if your system (and room) presents a somewhat dead sound that is also lush and warm, something as simple as a Topping D90 (which is ruthlessly revealing and harsh in some systems) may be better than a $15k tube DAC, or a Chord Qutest could fit the bill.  Or if your system is bright and very transparent, perhaps you’d prefer a tube DAC or NOS ladder DAC, for example preferring something like a DENAFRIPS Pontus to a Terminator.  Unless you don’t mind spending the money, I would recommend trying some of these sorts of DACs with various cables, do some quasi-blind testing, and hear if you can any differences.  If you’ve already done this, and truly want to ‘upgrade’, Soix’s questions become very relevant.  Have you checked out the DAC threads by users Verdant Audio and Mitch2 ?  There’s a huge sampling of different DACs and how they sound in those threads.  Lastly, consulting a good dealer like Verdant Audio, or another that sells Devore could be helpful.  As for me, I’ve tried a lot of DACs and with various systems over the years, and right now am using a $1500 DAC/streamer with no loss of enjoyment.  If I had a different system overall, a more expensive (or different) DAC might be appropriate.  

I replaced Aurender N200 Bricasti M3 combo with Meitner MA3i. Without a doubt it’s a superior DAC. But it also rendered N200 unnecessary. I’ve compared the internal network card in Meitner to N200 extensively.
I tested the N200 using native conductor app, as a Roon endpoint, with tidal connect and qobuz connect. Same high quality cables were used on both units - apple to apple comparison. I preferred Meitner as Roon endpoint point. Sold the N200. 
I will note though, that the N200 was a tremendous improvement over the Bricasti built in network renderer that I’ve been using prior to adding the Aurender. 

I have since migrated my library on an SSD to my Roon Nucleus One where it’s mounted inside the unit. 
 

I believe Meitner, EMM Labs, Playback Designs and dCS use the same roon ready network streamer from ConversDigital. Something to keep in mind when you’re shopping. 
Also, the most important and absolute critical part of shopping for a DAC is home auditioning for at least 2-5 days. Flipping back snd forth between dacs or streamers is not going to paint the correct picture for you.