Hello and thanks for playing!
1. For things like "Just an ordinary sword", you'll see that it's a single box. That means a single die only.
2. Correct, Ollie's effect only happens this delivery. On your next successful delivery, you only do what's on that person's card.
3. A delivery is made as soon as the token tracker on the Progress Tracker reaches the end. That means you may not necessarily do the Player Dice Upkeep step, which means you'll not have moved dice from Tired to Ready.
4. Ah, it should be written as where the token finishes its complete movement. So in this case it's 7 spaces, not individually 3, 1, and 3 with the ability to get the orange bonus multiple times.