This will only work if a hero may only have one kind of that item.
Make the item add a spellbook ability that adds the abilities the item should add normally on level 1.
On level 2 of that spellbook ability make it add also the ability you want to add to the item with triggers.
Now whenever you want to add that ability to the item, increase the level of the spellbook ability for the hero that has the item.
Make sure you do that each time the hero picks the item, use a custom value to the item so you know which item has increased abilities. |