The question, Is this worth automating?

No-one likes to do repetitive tasks. Well, perhaps some people do, but programmers should not. We like to automate the tasks. But when should we not? The stock answer would be to turn to a return on investment calculation.

However, I'd suggest that even if a task could be done manually in 30 minutes, where it would take 2 hours to script, you should automate it. If a process could be done in 5 minutes a day, but it would take 2 days to create a program to do it, write the program.

Why? Do you not care about your companies bottom line? Why, thank you for asking: Each time you script or automate something, you get better and faster at automation. What would have taken 2 hours to script the first time will take 1 hour the second, and a few minutes subsequent attempts. Consider what you learn in your decision to automate something.

And, of course, writing a script is much more entertaining than install the ruby devkit manually on 25 windows build agents.