There's a Dunmer waiting outside her office. At her approach, he stands at attention. 

"Lady Overseer," he greets. 

She pauses at his greeting. Hm. His appearance jogs her memory. After a moment, she recalls a conversation with her predecessor. She waves the Dunmer into her office, waiting for him to close the door before speaking.

"Agent Randon, I presume."

"Yes, Overseer." He stands in front of the door, his face wiped clean of emotion, "Reporting for updates to my orders."

"You are stationed in Windhelm, yes?" She asks, already knowing the answer, "Give me an overview on the situation there." 

So he does. 

 Ulfric Stormcloak has recently returned to the city after escaping his own execution. He spends much time in conference with his generals in the palace, which the agent can only rarely gain access to. What information he has managed to gather suggests they have recently gained a lead on the location of the Jagged Crown - an artifact which would grant whoever holds it a great deal of legitimacy as a potential High King. 

Racism against non-Nords is rampant in Windhelm, particularly against Dunmer, and less so against Altmer, oddly enough. The agent has managed to gain the confidences of several Dunmer who are highly placed in their own community, but there is only so much he can do with that given the circumstances.

Brunwulf Free-Winter and Rigel Storm-Heart are two of the most vocal anti-racism advocates. The agent suspects Storm-Heart will have an easier time getting Ulfric to listen than Free-Winter, if only for his connection to General Ragnar Storm-Heart, his father. It is a worl in progress, however, which could easily be derailed through any number of avenues available to the Embassy, should she desire. 

The Argonians in the city mostly work at the docks. They are expected to work long hours for a pittance, which they must as nowhere else will hire them. Some have taken to stealing some cargo here and there. He expects they could be paid to smuggle in anything they migbt desire to be brought into Windhelm. 

There have been several murders in the past few months, the work of someone the citizens have begun to call the Butcher. Whoever they are seems to be targeting young women, mostly. One of the daughters of the Shatter-Shield family was a recent victim. 

A young boy who's family was killed last year recently returned to the city and took up residence in his family's house. Rumours have been circulating that Aventus Arentino, the child in question, has been attempting to contact the Dark Brotherhood, his purpose unknown to the agent. 

 He continues on in this vein for a while, eventually wrapping up by mentioning that Windhelm is home to number of beggars, both adults and children, who could be made to work enthusiastically towards the Dominion's goals with the proper aplication of food and coin.