Here's a brief example of how overthinking can be counter-productive.
For no particularly useful reason, I read this StackExchange question today. The poster wanted to know how to produce an effect mimicking badly scanned medieval documents. It isn't a difficult thing to do with simple graphic editing software but there's a thin line between mimicry and the real deal. This, however, was my favorite answer:
Design your mark, then take it down to Kinkos. Find the crappiest photocopier, and make a copy. Then make a copy of the copy. Then maybe crumple/uncrumple the copy and make a copy of that. Continue until it looks the way you like it.
It's a bit like that likely-apocryphal story about cosmonauts and writing implements. Sometimes, even in everyday life, a complicated solution might not be worth it, especially if the simple solution is practically trivial to implement.
The complicated solution, of course, may be easier to automate. There are always tradeoffs.