Can you use 2 upgrade cards that read- When you reveal a dial.....? Which one goes first, do I choose the order?

Yeah, if you have two upgrade cards with the same timing, you can choose the order.

Yep. However, since Garm gives a ship the maximum tokens it can have, when you gain a token from Raymus you will have to discard one.

Garm Bel Iblis (if that is who you are talking) about doesn't trigger when you reveal your dial, his effect happens at the start of the round before you pick a ship to activate.