When you design your custom items, categorize them.
ie: Weapons --> Permanent Armor --> Artifact
Then in your trigger; let's say your unit picks up a sword. You would loop through his inventory to see if he is holding an item of classification permanent (Besides the item justed picked up) and if the unit DOES have one, then you know he has a sword...then you just make the unit drop the item.
Alternatively, if there is a large diversity amongst items (Shields, Sword, Ring, Earring, Necklace... ect.) then you can either do giant if checks (Terribly unefficient) or there's a few systems you can use like dummy color codes, item life ect.
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