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In my opinion your goal is to have the server down as short as possible.
So if you DONT upgrade the ODS while the server is down, you'll reduce your downtime.
The ODS conversion is nothing more than compact -c which you can schedule a week later, or even run in chunks at nighttime.
If you will run into any trouble it wont be caused by the ODS upgrade - it will be because any 3rd party applications (especially server tasks) are not compatible with Domino 8.5.
As long as you have not converted the ODS you can revert back to R7 pretty fast.
So clearly:
First upgrade Domino
Then enable any new features (ODS upgrade)
Feedback response number WEBB7VBMTQ created by ~Hank Dwotumisonynds on 08/27/2009