It would be nice to be able to configure different actions for the same alert based on different criteria.

For example, with the SQL Job failure alert - It would be very useful to be able to have these alerts go to X email address if the job contains "DBA" in the job name, and the alert go to Y email address if the job doesn't contain that text in the job name (This is just a basic example, being able to configure multiple of these types of filters would be the goal).

Right now the only possible way to do this is to configure a manual alert override on every job that fits that naming convention, on every instance, and continue to do this any time a new job gets added that fits that convention.

You can create custom alerts that would check the exact same thing as the built in alert, but send the notification how we'd want - The problem with this is that you're now doubling up on monitoring queries pulling the exact same information just to send a different alert which isn't ideal.

Having more flexibility for alert actions in Redgate Monitor would be a huge asset. There are several other suggestions posted here surrounding being able to do more with alerts such as to send alerts to different emails based on different severity thresholds, which I believe is similar but not quite the same (Ideally both suggestions would be added though).

Attached is what competing tool SQL Sentry can do for comparison - You can create unlimited actions for a single alert, each with customizable conditions and rulesets.