My path so far has been from the built-in DAC in the Bluesound Node 2i, to the Schiit Modi Multibit, and now to the Denafrips Pontus II, which is in the price range you specified. I am sure I will get the itch to upgrade at some point, but right now I am quite satisfied with the Pontus II. Because it sounds slightly different depending on which input you use, I opted for sending the USB output from my streamer to a Denafrips Gaia DDC to be able to drive the Pontus via its I2S.
I'm considering getting a streamer that natively supports I2S, like Magna's Manus mkIII or the new Mercury V2, eliminating the USB to I2S conversion. If anyone has experience with these or similar, I'd welcome feedback.