As is probably obvious I lied in the last updated when an idea for a solution to my problem came to my mind.
So I think I have everything setup. I am going to avoid going into specifics for security reasons but we now have much greater remote administration abilities that are no longer dependent on the server being online. I have also setup a range of automated monitoring software and utilities that will aid in both keeping track of site up time and doing some automated tasks that should allow the server to recover from all but the most serious of crashes automatically.
With that I am going to bed.