I found the source of my problem and it has to do with the settings that Outlook receives for Quota's. If Outlook doesn't receive a setting for all options then it will disable displaying quota's in both the file menu and at the status bar at the bottom of Outlook.
The solution was to make sure that all the DB Quota defaults had a numerical value. The field for disable send/recieve was configured as unlimiited. I tested by setting the value on just my account, after it worked I set it up on the DB defaults. It took just over an hour for the settings to show up on Outlook clients. I tried a fresh account, an account with the wrong info, and an account with a rebuilt .ost file. All of them received their correct mailbox size after the back end of Exchange updated.
To verify settings on my DB I ran a powershell cmd. You can also view settings from the Servers section of the admin console. Below shows all the fields I should of received on the client but I found through testing that the Unlimited option was what the client didn't like. If there's a way to view what settings the client received I did not find it.
Get-MailboxDatabase | select identity,IssueWarningQuota,ProhibitSendReceiveQuota,ProhibitSendQuota,DeletedItemRetention
Identity : AdministrationDB
IssueWarningQuota : 2.5 GB (2,684,354,560 bytes)
ProhibitSendReceiveQuota : 4 GB (4,294,967,296 bytes)
ProhibitSendQuota : 3 GB (3,221,225,472 bytes)
DeletedItemRetention : 21.00:00:00