Click here for more info on the East Empire Blessings and how convincing the Jarls works.
The following options are available for both Korir and Kraldar:
The book "A History of Winterhold" unlocks the Gift option and is provided by Korrin during the quest "East Empire Expansion".
The information needed to unlock the Gossip option is provided by the character labeled "Shady Contact". He will only speak to the player and provide the information if they equip the "East Empire Ring" provided by Korrin during the quest "East Empire Expansion".
If Korir is the Jarl, the note to unlock the Coerce option is called "Jarl Korir's Letter" and can be found on a dresser in the Jarl's bedroom.

If Kraldar is the Jarl, the note to unlock the Coerce option is called "Jarl Kraldar's Letter" and can be found on a table in the Jarl's bedroom.
