There's no way to configure the trigger to re-enable itself after a failure that causes it to be disabled. It seems like we should be smarter about this sort of thing, though, so I've written up an enhancement request to look into it.

I was going to suggest defining an exclusion period for this maintenance window so that the job is suspended during that time, but adTempus still evaluates triggers during an exclusion window and just defers execution, so your evaluation script would still run and fail. I'll also write this up as something to look into--maybe there should be an option to not evaluate triggers during the period.

You could simulate the same thing by scheduling jobs that hold this job prior to the maintenance window and then release it after some reasonable time. You can do this by creating a job that doesn't do anything by uses a Response with a Job Control Action that targets your email job, using the options to hold and release.