Not sure wether to post this in Dragonborn or Hearthfire, But on UESP, it says Teldryn Sero can become a Steward, but when I go to Heljarchen hall, He doesnt get the Dialogue to become my Steward. Are they pulling my Leg or is this a Glitch?

I couldn't do it. But mercenaries have been reported for several script problems when made stewards, so I'd pick someone else.