Thank you for your insights!
In terms of your damage question and whether it's the roll of 8+ damage or the dealing of 8+ damage - I believe it's the dealing of the damage. That would be consistent with other rules questions related to monsters dealing damage above certain amounts to damage character weapons or cause other effects.
That's kind of what I figured, it just seemed like it would be really hard to be in a second adventure without any sort of armour to mitigate at least two damage from counterstrikes. It feels like the boss is kind of neutered in that way considering that nothing else in the AP destroys gear to put you at a boss encounter without armour.
The other items are trickier - I don't think potions are worn. Backpacks and satchels - I can see these as being worn.
The concern I had here was that certain items (such as the Alchemy Satchel and the Large Backpack) facilitate the holding or modification of other items. In the Alchemy Satchel's case, it gives all potions a weight of 0. If the Satchel is considered "worn" and therefore "destroyed" are all of the potions immediately discarded?
Thematically, the potions would be stored in the satchel unless I'm way off in my assumption. Worst case scenario, you would have to discard potions down to your maximum encumbrance value, but in the middle of a battle do you have time to choose? Do you randomly discard? Are they all
"broken" too since the satchel is destroyed with them inside? I know that in certain scenarios when you are overweight, you can take time to choose and discard or use gear before paring down to max encumbrance (such as after drawing loot but before drawing the next dungeon card), but does mid-battle grant you the same luxuries? That is to say nothing of items stored in the Large Backpack...
It's little questions like this that give me AP. I've always appreciated official rulings to iron out the details, which I guess is what the community handbook is for. Thanks again!