Did you manage to get it to trigger?

I did in fact have trouble triggering the quest on one character, but I don't think that was level related. None of my chars have ever hit 81. My previous post was based on examining the quest conditions in the CK. For what it's worth, what I saw is that on every level up, a condition is checked to see if you have completed the precursor quest, are not currently in Solitude, and are at or above a level stored in a global variable. If so, it starts the second quest, and the first step of that quest sets up the courier.

If you were a PC player, I'd suggest manually starting the quest, but your profile makes me think you are an XBox player.

Did you read this: http://www.uesp.net/wiki/Skyrim:The_Man_Who_Cried_Wolf? I seem to remember that the "Go to the court" instruction triggers after we talk to the barkeep at the Blinking Skeever, when we ask him about rumours. I cannot check right now because my first character has already done the whole Wolf queen quests and the two others are brand new, sorry.