Syncing Ipad mail to Windows Live Mail on a Dell Laptop

I am trying to sync my boss's email through his multiple devices for him. He has an Ipad, an Iphone and a Dell Laptop. He has set up the email account (which is an imap account) on all the devices and it works from all of them. However, if he sends an email in one, it does not appear in the sent folder on a different device. How do I get the mail to sync so that every sent/received mail is visible from all the devices?
Also on a different matter, he also has an old pop3 account. Is it possible to change it to an IMAP account without losing the email address? Would I have to delete it and start again?
Thanks

Hi,
Actually I don't have any problems with mails and calendars as both of them work back and forth with Windows Live Mail and IPad.
The problem is only with contacts.  Once a new contact is created in my IPad it does not go in my Windows Live contact box.
Thanks

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