Lets stick to Chrysalis for now.
Since you’re on Linux, can you try installing the udev rules at Chrysalis/60-kaleidoscope.rules at master · keyboardio/Chrysalis · GitHub ?
Just copy the contents of those to /etc/udev/rules.d/, and reload the rules with sudo udevadm control --reload-rules.
My suspicion is that you may have permissions to write to /dev/ttyACM*, but no permission to write to the DFU device when the keyboard is in bootloader mode.