5 random/radiant jobs from Vex or Delvin per major city (minus Riften, makes 20).
Then 1 scripted quest per city.
Then tada ! you are guild master and are called boss

EDIT : This also allow shops to open near the Ragged Flagon with of course up to 4 of them and also increase up to 4000 the available cash at Tonilia the fence (wich makes her the best shop in the game as far as i know since she buys anything stolen or not and in large quantities).