Bedlam jobs take the longest to complete.
For bedlam jobs, you'll need to steal items worth a certain amount from a city. For fishing jobs, you'll need to pickpocket an item from somebody.
Since you're allowed to wander around in shops, these jobs are the easiest. For numbers jobs you'll need to manipulate a ledger in a shop. To restore the Thieves Guild to power, you'll need to complete random quests for Delvin and Vex, who can be found in the Ragged Flagon (#6): Gaining power for the guild is discussed below. The quests for the quest line will follow one after the other. After completing the quests, you'll be able to continue with the Thieves Guild quest line, and you'll also be able to restore the Thieves Guild to power. To join the Thieves Guild, you'll have to complete two quests for Brynjolf, who you'll meet in the Riften market.