I have only used transporter to move from 4.1 to 5.0, so I can't comment on how long the 4.0 to 5.0 move would take. I guess it is a matter of testing with a test user.
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Would it be easier just to reactivate everyone on the besx server rather than move them?
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That depends on what kind of user you have. We have lots of travelling users and many don't want to be bothered with re-activation, so a transparent upgrade without user intervention was much easier for us. But if you have all the users inhouse and don't bother helping them with re-activation, you would not need the transporter.