I have physically had the Grimm vs Antipodes. Grimm is lovely but has limited outputs (AES only) and is at its best upscaling. I don’t know the Canary DAC well. If it is best with a bit perfect signal that is not upscaled, Grimm is a poor choice. If it is a DAC that does well with upscaling like the Holo May, it is superb.
if you have a DAC that is best with a simple, bit perfect signal that has not been up scaled, Antipodes is maybe your best bet. The K50 would be spot on your price range and had many more output options. Because of the dual computers (one for server, one for player) it outperforms many other units with Roon.