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Well currently through Judge Daramid. She knew the Judge and she knew that the PCs were going to Lepidstadt to see her. So her initial letter (and the only one sent so far)was actually sent to the Judge's address. The Judge had the letter forwarded to the inn the PCs are staying at: The Brazen Skull (Rule of Fear source book).
Like I said, the Judge has played a much larger patron role in my game than as originally written (partially because I ran Feast of Ravenmoor with her as the contact and the party also likes her no-nonsense, stern contenance and attitude).
They are in Schloss Caromarc right now and as of now the player has only responded to the letter (not gotten another reply - I will be keeping the letter writing as realistic as possible in time frame as possible).
One thing I am doing is slowing down the events in the path. It makes me a little insane to imagine players going from 1 to 16 in a handful of months so I've been adding downtime for crafting and other threads (Feast of Ravenmoor, probably Carrion Hill)
The player is invested in continuing his contacts with Kendra and so my hope is that with the extra downtime he will either write her when he gets a chance or establish a place she can contact him at.
Like I said, I'm still just starting this letter writing chain. I'm trying to make sure that characters met in various of the books don't stay one shots but continue to guide and influence the story and provide additional background.
Oh god. This became a giant post. I'm done now.