#damage assignment order

Yes, this is fine. Just put the non-enrage creature first in the damage assignment order. You never have to assign damage to creatures beyond the first if you don’t want to.

So in your scenario, once you declare your blockers, the attacking player will choose a damage assignment order for the 3/3 so that you’ll know if it will deal damage to your 2/2 or your 1/2 first. (They probably want to kill that 2/2.) When the game moves into the combat damage step, they have to assign at least 2 damage to the first creature before they can assign any damage to the second blocker. They can also just assign all three damage to the first creature if they want to, of course.

As for why it works this way and not the other way, imagine blocking that same attacking 3/3 with a 3/1 creature and a 0/5 creature. If you got to choose which of your blockers would be assigned damage first, then you would choose the 0/5 and thus be able to pick off your opponent’s attackers with no consequences. The defending player already has the advantage of being able to choose whether or not to block and which creatures to block with, so allowing the attacking player to choose the damage assignment order brings the scales more back into balance. (It also more closely mirrors the pre-M10 system of being able to assign damage as you wanted across all blockers.)

Damage assignment order is only for when a creature is blocking or blocked by two or more creatures. (e.g. Wall of Glare in this scenario). When multiple creatures are assigning combat damage to the same creature, there’s no order to it. The total damage assignment just has to be legal. So yes, you can trample over for 2 here.

When multiple creatures block a single attacking creature, the attacking player chooses a damage assignment order for those creatures, i.e. they’re choosing that the attacking creature will assign damage first to a specific creature that’s blocking it, then if it can assign lethal damage to that creature, further damage can be assigned to the next creature in the blocking order and so on.

However, your opponent will choose which of your creatures will be assigned damage first, and lethal damage has to be assigned to that creature before damage can be assign to the next creature in the damage assignment order, and so on.

Damage assignment doesn’t take damage prevention effects into account when determining what counts as lethal damage. Because the attacking creature has deathtouch, your opponent can still assign 1 damage to each of the blockers to kill the second bear.