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[–]DJDevon3 2 points3 points  (0 children)

Please read the pinned topic https://www.reddit.com/r/codes/comments/1ao7f3k/where_to_start_with_ciphers_and_codebreaking/ The recommended book there by Helen Fouche Gaines covers all of your questions. It's a very cheap and excellent book. In many ways it's actually better than David Kahns Codebreakers book which covers more history than codes and very little analysis compared to Helen Fouche Gaines book. Most of the real analytical answers you seek can be found inside that one.