Microsoft Account/s and Outlook 2013

Please advise on this scenario:
John's email is hosted on a Smarter Mail Server [email protected]
John buys a new Windows 8.1 laptop with Office 365 installed and signs into his Microsoft account using his email address
[email protected]
He gets an Outlook.com account [email protected]
He sets up Outlook to connect to his Smarter Mail server via IMAP
He adds his old Outlook 2010 PST data file archives to Outlook 2013
John's Windows Phone was set up by the phone shop last year with a different Microsoft account
[email protected] where all his contacts are stored
He adds an Exchange Active Sync account to Outlook 2013 to get his contacts from
[email protected]
This is causing all sorts of problems. OST file errors. Incompatibility with Outlook 2010 PST files. Non-syncing of contacts etc.
How can John get all his mail, contacts and apps into one account across all devices - preferably his main Microsoft account
[email protected]
He does not want emails labelled "Sent on behalf of"

 Per your post, this should be the Topology, right?
In general, this operation is normal and wouldn't cause the issue you list. However, we still occur the following issue:
1. OST file errors.
2. Incompatibility with Outlook 2010 PST files.
3. Non-syncing of contacts etc
For one, IMAP and EAS profile also use OST file as the data file. The problem appear since you add the Windows Live account into your profile, so I guess the root of issue is caused by Windows Live associated OST.
For two, please view this:
http://support.microsoft.com/kb/839109/en-us
Another thread may also help you:
http://answers.microsoft.com/en-us/office/forum/office_2003-outlook/outlookpst-is-not-compatible-with-this-version-of/719c8cf1-a699-4ee4-ae63-8993489bc422
For three, IMAP doesn't support contact sync. The problem is also related to Windows live account, I would like to know if you receive the email through live account smootly, check if there is any sync issue log in the
Sync Issue folder
At last, you may totally create a new profile to check the result of Problem 1&3.
Cheers,
Tony Chen
Forum Support
Come back and mark the replies as answers if they help and unmark them if they provide no help.
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