Command lines? Yes we use them and have to for our Remote Support function utilizing an SSH connection that is encrypted for outbound only (TCP port 65500). But from end user standpoint we do not allow for this and as you stated, like your boss, realizing the value in simplicity with a product can provide benefits with additional administration knowledge.
We never had to fly out the next day in all the years Open-E has been in operation; usually we provide this support remotely as stated before. Most of our resellers provide response times that you might require; you might want to check with them although this will require additional cost as with most industry companies do charge for this. I am sure NetApp, Falconstor, Wasabi, EMC, Microsoft and others do not provide this for free as they use in conjunction with resellers to assist for cases of 4,8,24 hour onsite response times.

You can update the modules from any pc and then place back into the USB header pins of the MB. When updating make sure you select option 1 to keep existing settings. And as always like any OS save your configs and setup located in the Maintenance > Miscellaneous. Also save the config locally and on your system as well.