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I am now on level 32 and am looking for Sam Guevenne to start this task. However, I have just read that sometimes due to a bug, Sam may not appear in any tavern located throughout Skyrim after reaching level 14. The reason for this is unknown. I am on xbox.
I found him in Whiterun, just a random thing got me drinking with him. I'd seen the guy before but just ignored him. I was easily 14th level. PS3
Try not to read too many spoilers
One report is that he will appear in the city that was closest to you when you reached level 14. Known locations include Whiterun, Riften, Winterhold, Solitude, Rorikstead and Ivarstead.
Thought you could only get this once you were level 41, not 14. Then again, I'm dyslexic so I could be wrong. However, right now I'm level 48 and I just ran into him a few days ago (I'm on a 360) and got the Sanguine Rose which I love. He was at a bar in Riften when I was handing out pamphlets for Mara.