[@DepressedSoviet] I'll say to this to everybody once. Anything can work, but you have to remember the mantra of [i]why are they here?[/i] every step of the way. This is, essentially, a covert military undertaking by the Empire entrusted to Sibassius. Creating a plausible reason for him to take your Dunmer bureaucrat with him is key.

That said, it just occurred to me that disguising the whole mission as an eclectic treasure hunting expedition isn't a bad idea.