but honestly I would verify that the firmware update works on a Mac first… maybe check the GitHub for the firmware updater and see if anyone has successfully done it first. I know you can run docker on OS X and what not… but you may be risking bricking your stick if it doesn’t work.
Ok, I could be totally wrong and it may work perfectly on a Mac, but I myself would go with a Linux install… just because OSx while in a very generalized term is the same, there are a lot of quirky dependency things and stuff that I have ran into.
do you know how to ssh into your pi? What type of HA install is it?