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1) You don't need to serve time, as escaping is also an option. Also you don't need to get thrown into jail at all, as there are 3 other ways to get into the Thieves Guild:
- play detective and ask around about the Grey Fox after reading his wanted poster, eventually the beggars will direct you
- you can get the info from City-Swimmer in Bravil by using the correct dialogues
- you can also just speak to Armand Christophe at night, if you raise his disposition high enough he will drop the charade and allow you to take the test
2) You don't need to get the Diary to get in. If you fail the test Armand Christophe will give you a second chance, where you will be tasked with stealing Rohssan's Antique Cutlass from a A Fighting Chance.
What you are doing is first timer mistakes and you are expecting others to follow your lead.