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1) Yes, I passed off the dagger when I originally became an assassin. 2) Yes, I'm playing unpatched.
When this bug occurred, I declined the offer to become an assassin again because I was worried about it messing up my character.
However, I then went to a slightly earlier save, and this time accepted the offer. The journal listed my character as a level 10 (or so) assassin, AND a level 1 assassin. He needed 1500 hit points to level up. I didn't experiment any further, though.
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