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In other words: Do I have to update both my Macbook (from where I manage the remote OS X Server) and the Mac Mini (where the Server is actually serving) to Yosemite and OS X Server 4 at the same time?

What do you mean: "Nothing can go wrong: all your Keychains; SSH keys; Certificates; Open Directory settings; web apps; .... will migrate just faultlessly."?

I think my strategy will be to upgrade the Server machine first and only manage it locally until I am sure it's working perfectly. (Not an option for those without local access to their OS X Server.)

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No you can't.

  1. Server 3 won't run on Yosemite.
    So management of remote Server 3 is not possible with Yosemite client.
  2. Server 4 client on Yosemite alerts that it "will only connect to remote OS X Server running on OS X 10.10"
    In other words: both Server client app and Server server need to be at Server 4 on OS X 10.10 if either end switches over to Yosemite.

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