My plan is more to make it "does it make sense that the character would leave his/her equipment?" So, the people in the shipwreck won't leave their equipment, because why would they stop to take all their armor off before falling off the boat? Every time Kain leaves it is sudden and "unexpected," too, so he won't leave his equipment. Cid, however, is like, "I'm gonna stay here in the dwarf castle for a while, see ya later!" So it makes sense that the party would be like, "OK, but can we have all those weapons and armor back that we spent all that money on?"
Tellah dies right in front of you. It's kinda weird, but the party could choose to take his equipment off before they move on to save Rosa.
So I'll be looking at each departure and deciding if it makes sense story-wise that they might leave their equipment benind.