Cyseal doesn't have a blacksmith any more (boarded up his house and left), so the highest level repair an NPC can do is 4 (Wolfram, the lost archaeologist).
The number of wins required depends on your charisma and conversation choice (sometimes there will be a situational bonus or penalty depending of your charms/intimidate/reason choice).
Yes, you can buy a spell book to learn the ice summon later.
