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This hits home. Manytime have I come to appreciate a library or technology only after delusionally attempting to create a 'better' version. Mid attempt I actually start to understand the problem space, at which point I humbly and thankfully start depending on said library or technology.

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Yes, I very much see myself in this. Though rather than humbly depending on the library, I tend to wander off in disinterest. I realize that my motivation came from saving the world with a supposedly better solution, and I didn't actually care that much about solving the problem in the first place.

What kind of problem spaces need so much trial and error to understand?

https://xkcd.com/592/

What does this comic have to do with the topic?

Did you read the alt text?

That looking at almost any problem and thinking 'this seems simple?' is generally an indication that you have MASSIVELY underestimated something.

In other words, that by asking the question 'What kind of problem spaces need so much trial and error to understand?' you are betraying a sort of charming naiveté.

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