First question: yes, Cross bow bolts count as improvised daggers in melee.
Considering I once had a samuri who carried 7 katanas (his father's his grandfathers' and his great-grandfathers') who combined quick draw with the fact the dropping a weapon was a free action to iaijutsu full attack his enemies thanks to his two weapon fighting skills, then the second question is yes, but a reasonable DM would make you get Quick Draw if that's your fighting style, the third question is a yes, assuming you have the weapons.
As for the fourth question, I believe it's an Iaijutsu damage bonus, since I remember one creature in OA who was immune to Iaijutsu damage.
The real question is, how many ways can you make your opponent flat footed once the battle begins.