Just curious why someone who has experience with LinuxCNC would use word 'difficult' at all? I've partially working setup of MachineKit on RPI2 with software generated step/dir-pulses and it was like nightmare...
I'm using bCNC under Raspbian on RPI 2/3(also on Windows but that was long time ago), all avaiable ports are detected automaticaly on program startup, so it's simple as selecting it from drop down menu. You should check if your Nano was detected by the system and ttyUSBx devices were created, check dmesg. I've chinesium Nano and it's detected only if I replug it after system startup. I think when my router was running on UNO-clone everything was detected without any needless actions.
bCNC is like only one who has working macro's for M06 tool change commands and [partially] working g-code editor, it's super handy when working on PCB's.
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chilipepper could be OK and useful for headless setups, but support for grbl interface is almost non-existent so if something happens you could count only on yourself.