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How long did it take for you?
I tend to ignore them anyway, because I stumble on the relevant quests anyway.
You said it worked in your previous post.
Dont try to 'force' it. It is one of those things that will happen when it happens. There is no 'formula' to make it happen predictably.
That's because you have to wait for the courier to actually walk to your location. When you fast travel they basically fast travel to the same location; that's why they run right up to you. If you just walk around the province you can meet them on the road and so on.
Why are you so hellbent on getting that generic letter anyways?
And that's when I first started this thread. When I started my first game, I saw on the wiki that a courier should be showing up. I had no idea what the letter would say, if it would unlock 5+ hours of content, or if would be a reference to another Bethesda game, or what. I didn't care. I wanted it no matter what it offered. Because this game does that to you. I gets you mesmerized and wanting to experience it all. Even if some of it ain't worth jack.
Yes it worked.