I think looking at the WEBountyCollectorQST would be a perfect reference point for you to start from. It may help you learn more about the system than having us explain exactly how to do it, step by step. Look at the quest scripting in particular. To make the quest advance when sleeping in a bedroll, you need to add a script to the bedroll object that extends ObjectReference, and includes an OnActivate event. If you are still having issues after looking at that quest, reply!