A couple of questions I don't see on the list:

Will writing the script be fun/rewarding? (arguably related to the "Will I learn something new?" question, but not exactly the same).

Will doing the job by hand be soul-crushingly boring?

There are long-term quality of life/job satisfaction metrics that aren't necessarily apparent when you only focus on the task at hand. :-)

Almost always, yes. If you script everything all the time, even if it takes you longer, twenty years later you'll be able to script anything so fast you'll be so productive your head will spin.

It's like learning Vim. :)