Philip Brindley I was away on PTO on Friday and just back in the office today. They requested the accounts that this is happening on for me on Friday and I supplied it to them. No word back yet but I will request a call back for this afternoon. One thing I know for sure is that the surface pro requires you to be on your internal network. Initilaly I had them connected to a guest network but after speaking to my colleagues they suggested connecting them to our corporate internal network. It didn't change anything on the new room accounts that cannot fetch, but it did affect the old acounts that do work. With the old accounts on a guest network it could not fetch the calendar, when on our internal wireless it worked just fine. It's weird because we are 100% in the cloud now, but it still needs our internal DNS servers and connection to AD I guess?
We have 5 new room accounts, the old room account that is working in another site is listed as "Synched with Active Directory"(in the O365 admin center), because it was created pre-move to O365. While all new accounts are listed as "In cloud", so I created a new user account and specified the email address in our internal AD to test. After forcing a dirsync and waiting like 5 minutes it showed in O365 admin center that it was "Synched with Active Directory". Unfortunately this had no effect on the fetching of the calendar. This was done last Thursday.
update: It seems they are escalating my case to a higher level.