You seem to be an expert.
Any words of wisdom about making Samba to automatically run on start-up and also automatically mount attached USB drives?
Basically you can't. This issue was discussed in the earlier posts in this same thread:
pogoplug doesn't have a BIOS to detect the USB devices that are connected at boot time for boot order designation. It's up to uboot (the boot loader for arch) to choose which drive will be the /dev/sda1 (or whatever the device assigned for / ) when pogoplug gets turned on. It can be the correct one but most likely it's not (otherwise we wouldn't have issues).
With the pogoplug models that come with an internal SATA port(P21, B01) there is a solution for activating the boot code to use the SATA device as the 1st device everytime but since those pogos are oxnas chip based, they are still using linux kernel 2.6.x and no systemd support. I am not saying systemd is much better than sysv/rc.d but in order to get the perfect boot everytime, you will have to find a way to get a SATA drive connected to the pogo (power and all), modify the code (archlinxu forum), and be ok with only 128MB ram for those pogo models.
I would rather just stick with the E02 model that has 3.x kernel and systemd support. And if I really need to reboot the server I will just have to live with unplugging all drives except for the system drive and inserting them back in afterwards.