Did you take a zeppelin to Aleroth, or head back to Broken Valley or Sentinel Island? I don't recall how much of a delay there is before Crabbe gets to the top of the harbour building; you might need to change map areas, or just come back later.

The two one handed weapon skills are independent (they do not interfere or compliment each other). Using a one handed weapon, if you equip a shield the 'Sword and Shield Expertise' skill will be used, otherwise 'Single-Handed Weapon Expertise' will apply.