Highlighted quests can be easily completed without any skill use. You can also befriend merchants if you have the Investor perk by investing in their stores. If they die after you assist them, they still count towards your Thane status. Note that many of the quest givers are non-essential NPCs, so their deaths would result in a loss of potential quests to complete. You must assist three people in the hold, usually by completing favor quests for them. Once you have completed the prerequisite, speak with the jarl again and he will ask you to assist the people of the hold. If the jarl is Kraldar, whether he was installed via Season Unending or Rescue from Fort Kastav, then the completion of that quest is sufficient to fulfill the prerequisite.
If the jarl is Korir, then you must usually Retrieve the Helm of Winterhold for him first however, if he was ousted from Winterhold during Season Unending and reinstated following The Battle for Fort Kastav, that is sufficient to begin this quest.
In order to receive this quest you must first aid the current jarl. This is an umbrella quest for several other quests that must be completed to become Thane of Winterhold. The jarl lives at the Jarl's Longhouse in Winterhold. This is a radiant quest that you can receive from either Korir or Kraldar, whichever is the Jarl of Winterhold.
