No. You do not have to go through that for each device.Check out one time, then copy that folder of data and paste it onto each device. Simple as that.
So I guess the real answer to your question is yes, each device will need their own checked out version of the feature class. Ideally, after you check their edits back into the geodatabase, you check out a fresh version of the data (so the changes from all of the other versions are included) for each device.
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