Building Puzzle

A certain street contains 100 buildings. They are numbered from 1 to 100. How many 9's are used in these numbers?




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=> You can only use addition.
=> For making a number, two single digits can be combined (for example, 4 and 2 can be combined to form 42 or 24)
=> A fraction can also be made by combining the two single digits (for example, 4 and 2 can be combined to form 4/2 or 2/4)

Question: how can we do this?

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Amazing Facts

Challenging

There is a cryptic organization called Cicada 3301 that posts challenging puzzles online, possibly to recruit codebreakers and linguists.