I'm not familiar with the DAC, but you can't go wrong with those Kali Monitors or the JBL Subwoofer.
IMHO, the monitors do not sound dry or flat, and they are quite musical. They have good bass response, but the JBL Subwoofer will definitely be a good addition.
I use Adam T5V monitors with an Adam T10S subwoofer in my office setup. (I preferred the Adams to the 1st Gen Kali LP6 monitors back when I was looking to buy, but it was by a narrow margin, and came down to personal preference). An Audient EVO 4 USB audio interface is used to play them from my laptop. I'm very happy with how this combo sounds, and wouldn't change anything.
Laptop USB > Audient EVO4 > Belden + Neutrik Balanced cables > Subwoofer > Belden + Neutrik Balanced cables > Monitors.
I can also directly connect the Audient interface to my iPad Air (5th Gen) to the EVO4 via USB C to USB C cable.
If you need Bluetooth connectivity, you will need a DAC that has Bluetooth input. I don't think there are any commercial Studio USB Audio interfaces with Bluetooth input, at least in the under 20K range. (I could be wrong here). Generally (personal opinion), I think that in the 12k to 20K range, a commercial USB studio interface from Audient or Motu, or even Focusrite would be a better choice than a ChiFI DAC. But, you will not get Bluetooth connectivity.
One thing you will have to consider (since this is a nearfield desktop setup) is that these are fairly large speakers for a desk-top, Do check if you have space issues. My monitors are slightly smaller, and I have them on stands (regular, non-fancy studio grade stands).