Does the item stealing occur before or after the Knock Off damage calc if it does? Since Weavile gets both, I was wondering.
Nope!
Knock Off does amplified damage, the item gets removed, but the Pokemon doesn't pick up the item with Pickpocket.
In Pokemon Showdown: On consecutive turns where Knock Off is used on a Pokemon that has Pickpocket, a 'ghost item' will appear and immediately get knocked off. The ghost item has no effect.
Source: Here
When you use Knock Off against a Pokémon with the Pickpocket Ability that is also holding an item, Knock Off will just knock off their held item.
If you used Knock Off against a Pokémon with the Pickpocket Ability when they don't have a held item, the Pickpocket Ability will activate saying you have gained the targets item, but immediately after saying that it says the item was knocked away by Knock Off. So basically you gain the targets held item but immediately lose it.
Source: http://replay.pokemonshowdown.com/ou-92890182
Hope I helped :)