The term "dark art" is usually used in these parts to mean something very different from this...
[EDITED some time after posting, to fix a typo.]
[EDITED again to add: when I wrote the above, the title was something about "the dark art of estimation"; it's been changed now. This also explains Dr_Manhattan's otherwise confusing question.]
I strongly recommend the street fighting mathematics book. It is short and full of good stuff.
I end up helping otherwise smart people with techniques from this book all the time.
Here it is in PDF. http://mitpress.mit.edu/books/full_pdfs/Street-Fighting_Mathematics.pdf
The link is broken. Seems that MIT has an e-book storefront and understandably wants to charge for the electronic version.
This is a good post, but you should change the name or people will downvote without reading.
This is a Link to a resource I came across for people wishing to teach/learn Fermi calculation it contains a problem set, a potentially useful asset especially for meetup planners.
Has anyone had experiences in which similar reasoning was useful?
I suspect it is, and often, for someone with this mental habit. I lack this habit, so I don't easily know what opportunities I've missed. I'd like to teach the habit to myself and others, but I will need a handful of motivating cases.
Fermi problem
Link: en.wikipedia.org/wiki/Fermi_problem
Fermi Problem: Power developed at the eruption of the Puyehue-Cordón Caulle volcanic system in June 2011
Link: technologyreview.com/blog/arxiv/27140/
If you want to get better at doing rough mental calulcations, the following books might provide some valuable heuristics:
Street-Fighting Mathematics: The Art of Educated Guessing and Opportunistic Problem Solving
Link: web.mit.edu/newsoffice/2010/street-fight-0329.html
Secrets of Mental Math: The Mathemagician's Guide to Lightning Calculation and Amazing Math Tricks