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There are some really clever people here, but as a general rule, you can't truly automate something until you can do it manually to the point where you're fully aware of all the snags and exceptions that may occur.

Once you reach that point, it then becomes a matter of trading-off how much time/money/effort it will take to automate the task against what benefit you get in return.

Agreed, but it's important to include one criterion in the trade-off calculation: I'd much rather be writing automation code than doing most automateable tasks (i.e. repetitive, simple decision tree). Even if I don't save any time, or even if it actually costs me a little time, I count it as a win. Especially since I often discover useful tools and techniques (holy smokes! Someone already wrote a parser for this weird thing I'm playing with!) that end up being valuable later in a completely unrelated project. True story: some colleagues wanted to integrate a departmental Moodle server with some bespoke scheduling software we were running. Turned I already had most of what we needed, because a year earlier I'd gotten irritated at hand-loading class lists into Moodle and hacked together a bunch of code to directly translate entities from one database to the other. I'd even generalized it into a bunch of types and tables that I didn't really need because OCD. All that 'hobby' code ended up being really valuable later.

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