Reach Wood Side Apartments.

Try to leave Silent Hill in the Observation Deck area.

Complete 10 side quests

Complete "The Fallen"

Capture Solitude or Windhelm

Complete "Hail Sithis!"

Join the Dark Brotherhood

Complete "Elder Knowledge"

Defeat all enemies in Mission 01 as Nero, Dante, or V.

Complete "Revealing the Unseen"

Complete "Glory of the Dead"

Read 50 Skill Books

Pick 50 locks and 50 pockets