Hi,
Sorry for the late response here, our goal is to not have any delays here, but we really can predict yet how long the upgrades will take. So it may be that there won't be any delays at all, that's what we are aiming for, but we don't know untill we are upgrading ;).
If there is a delay, we will run all the other updates in succession where possible, without any delays between the different steps.
In the case of a downtime, transfers will be frozen and the deadline will be moved forward. No transfer will end during a downtime, they will also be delayed.
And yes, we sure hope and expect all offseason processing will be completed soon enough to give you enough time to prepare for the new season.