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MIT OCW has a free textbook "The Art of Insight in Science and Engineering: Mastering Complexity", which I usually point folks to on the subject of estimating physical systems. I think this is a real gem. Another work of the author is referenced at the bottom of the article. I'll also vouch for the referenced Guesstimation (though I hate the title).

https://ocw.mit.edu/courses/res-6-011-the-art-of-insight-in-...

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There is also Guesstimation 2.0 by the same authors which is a sequel to Guesstimation and is just as good.

Also see Maths on the Back of an Envelope: Clever ways to (roughly) calculate anything. by Rob Eastaway - https://aperiodical.com/2019/11/review-maths-on-the-back-of-...

Related is How to Read Numbers: A Guide to Statistics in the News (and Knowing When to Trust Them) by Tom Chivers and David Chivers - https://en.wikipedia.org/wiki/How_to_Read_Numbers

Finally, the old Soviet books by Yakov Perelman (https://mirtitles.org/?s=Yakov+Perelman) named Physics for Entertainment, Mathematics for Fun etc. also fall under the same category and are a good read.

Bonus: https://en.wikipedia.org/wiki/Back-of-the-envelope_calculati... Follow other links like "Guesstimate" from the "See also" section.

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