- How likely is it that you will make a mistake when performing the task manually, and how easy is it to fix the various mistakes that can be made?

- How likely is it that you'll overlook the task when the time comes? (e.g. SSL cert expiration)

- What are the costs of mistakes or failure to complete the task?

- What skills can you learn while developing the automated solution?

- How can techniques developed for the automated solution be reused for other tasks?

Of course it's fair to ask questions on the other side of the equation, too, like: if the automated solution goes bad, or is run in the wrong environment, what are the risks?