[willyvereb]

1.) He's there...you haven't played with the game for a long time. Right? The only difference is who will destroy the Grail.
2.) I don't know. Seriously it's the greatest mistery of the whole game.

Spoiler for speculation:

Fate means fated encounter or it was fated for Shirou to join the war. Stay night means the nights are long because every battle happens at night(or mainly at night).But it's still mysterious.