There is a great XKCD comic, is it worth the time, that displays the maximum amount of time you can spend on a project before the payback is more than 5 years, depending on how often you do it, and how much time you save each time you do it.
While it is a good rule of thumb, there is a missing dimension to it:
Irritation factor: How annoying is it to do the task each time?
Working on a project this afternoon, I had to do a series of steps multiple times. To automate it probably wouldn't save much time, I am unlikely to need to do these steps again after I finish. And yet, the process was tedious and just generally horrible.
I haven't automated the whole thing, but some steps have been, and it has helped.
I don't know if I will have saved time in the long run, but I have certainly made my job easier and more pleasant.
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