I was asked earlier how many closing brackets in a row I'd written in Mathematica. The challenger presented a the end of a line with a hefty ten consecutive brackets, closing functions, array references, and lists.
I did not know if I'd beaten ten. I could spot fives and sixes in my open document, but not much higher...
I wrote some code to import the plaintext of my 'archive' folder, which contains a lot of notebooks, and answer the question for me. The results of naive character tallying across notebooks are quite interesting. for example I (somewhere) have six sets of unclosed square brackets, representing a 0.005% square bracket closing failure rate! I didn't manage to beat or match 10 brackets, but I've used a string of nine brackets on twelve occasions.

Pictured above: The occurrence of strings of bracket characters in my notebooks.
Pictured below: The occurrence of different individual characters in my notebooks. (Open image separately for higher resolution)

I'd be interested to hear these arbitrary measures for other peoples old notebooks. Can you differentiate peoples coding styles from such simple metrics I wonder. Notebook attached (you'll need to specify a directory containing notebooks to run it on).
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