Magic The Gathering - Jace, Cunning Castaway's +1

Question

I'm confused by this ruling for Jace, Cunning Castaway:

The delayed triggered ability created by Jace’s first ability can trigger more than once in a turn if creatures you control deal combat damage at different times in a turn (most likely because one or more has first strike) or if creatures you control deal combat damage to more than one player at once.

I'm not sure because of it saying it can trigger more than once if creatures do combat damage at different times.

If I activate Jace's +1 Ability and attack with two creatures, and both do combat damage in the same combat damage assignment step, do I draw two cards or one?

If I attack with two double strike creatures and they both do combat damage, do I then draw four cards?

Answer 1

You draw cards equal to the number of combat damage steps where your creatures have dealt damage.

If you attack with any number creatures, none having first strike or double strike, there is only one combat damage step. The delayed trigger will be met once.

If the creatures you control do damage during the first strike and the non-first strike combat damage step (eg. a creature with double strike or mix of creatures with and without first strike), the delayed trigger will be met twice.

If you have multiple combat phases during the same turn, the delayed trigger will be met once for each non-first strike and first strike combat damage step that occurs.

Combat damage is dealt all at once (or in two steps if you have first/double strikers) instead of once per creature. To break it down (simplified) combat looks like this:

1. Attacking Player declares attackers
2. Defending Player declares blockers
3. Combat Damage Step (Comp Rules 510):
   a. If at least one creature has First Strike or Double Strike, only creatures with first strike or double strike assign damage this step.
   b. Players announce how their creatures will assign damage (eg. Attacker is blocked by multiple creatures, trample etc.)
   c. All assigned damage is dealt simultaneously. (Jace's Ability Triggers here).
   d. If this Damage step was for first/double strikers only return to step 3.b but this time all creatures except first strikers get to assign damage. If not proceed to step 4.
4. End of Combat Step

Answer 2

I know this is very late, but I felt since no one else had said this, I should. In addition to the top posters scenario, the ruling also seems to make it clear that if you are in a game with multiple opponents and your creatures deal damage to more than one opponent. For example, if none of your creatures have first strike, and in the single combat step your creatures deal damage to 2 opponents, you should draw 2 cards, not one.