Migration from Exchange 2007 to Office 365 - Failing

Let me preface this by saying I am not a System Admin; my specialty lies in networking.
I work for a small ISP with ~22 employees. We are looking to ditch our old Exchange 2007 server (running on Windows Server 2008 SP2) in favor of moving everything to the Office 365 cloud. I'm almost there, except Microsoft is failing to connect to our server. I am trying to do a Cutover Migration. Here is the exact error I am getting when running Microsoft's Remote Connectivity Analyzer:
Testing HTTP Authentication Methods for URL https://mail.server.coop/rpc/rpcproxy.dll?SERVER.server.local:6002. The HTTP authentication test failed. Additional Details A Web exception occurred because an HTTP 404 - NotFound response was received from IIS7. HTTP Response Headers: Content-Length: 1245 Content-Type: text/html Date: Mon, 22 Feb 2016 20:36:02 GMT Server: Microsoft-IIS/7.0 X-Powered-By: ASP.NET Elapsed Time: 114 ms.
I have been making good use of The Google today trying to find a solution. I've verified the RPC service is installed and running. I have restarted IIS (we're running version 7), verified Outlook Anywhere is running, checked that C:\Windows\System32\rpc\rpcproxy.dll existed.
I've checked to be sure port 6002 was open and it is; I had also disabled the firewall on the local machine to no avail. I'm at a loss and I only have a few more hairs to pull before I go completely bald. Any insight on this would be greatly appreciated.

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Claymoore

Office 365 requires Outlook Anywhere for a connection to the mailboxes to migrate them. Outlook Anywhere was previously called RPC over HTTPS. You need to make sure that you have the RPC over HTTPS feature of IIS installed and enable Outlook Anywhere in 2007.
https://technet.microsoft.com/en-us/library/bb123889(v=exchg.80).aspx

For best results, follow the instructions in the Exchange Deployment Assistant