I am going to be migrating a client from SBS 2003 to Windows Server 2012 R2 Essentials for onsite file and server functions and Office365 for Mail/Exchange. The question I have is whether I should configure Office365 to use directory synchronization (available in the Midsize business package) or Small Business Premium which then keeps the internal server and cloud services separate.
My first instinct was to use the directory synchronization for less management (single sign on, password,etc.). But the more I read, the more warning I see about how this is a very permanent design choice, user configuration can no longer be done through the cloud interface, and is more complex to manage.
There are only 15 users max, without a lot of turnover, so it wouldn't be too much management if there are two user account lists.
For those that have taken on Office365 what is your suggestion.