This question boils down to how to handle failures in db and application upgrades, and which one should be done first.

If it is critical to keep the downtimes as small as possible, I would try to split the deployment into the following steps:

1. Set the applications into "read-only" mode for a short time to prevent data loss (you may have to implement such a feature).

2. Make only changes to the DB like adding columns and tables which are "backwards compatible enough" so the old application version can work with them (at least in read-only-mode). Even an operation like "split a column into two" with some data migration is possible here, as long as the original column is not deleted right now.

3. Then, upgrade the applications. Any application which was updated successfully can be switched to read-write-mode again. If one application server upgrade fails, fix the issue (or take the server offline). Don't proceed until all running applications are upgraded.

4. Make the non-backwards compatible changes to the database, like deleting tables or columns which are not needed any more.