So while this is absolutely ancient tech and process by most means, it has been a huge step up from copying files over to machines by hand through RDP connections.
And also, our apps have no problems having even a few minutes' downtime, so cold restarts are absolutely fine for us.
While I would absolutely like to get into containerized zero downtime deployments, from where we're actually standing now, those don't seem to be offer much in the way of ROI.
And please, if anyone has a more suitable process in mind, please let me know!