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I have never used the tears to kill him. Just have that guy with the gatekeeper arrows help you and go kick the gatekeepers ass. The quest will just skip the tears part of the quest and update after you kill it.
Are you using any mods? There are a few items in the game that are invisble to the player. They are usually armor that are not supposed to be equippable by the player. Maybe whatever makes those items invisible is happening to other items. I have never read about anything like that happening though.
That is one reason why it is always important to save your game often and keep multiple back up saves.
You never know when you will have a problem with the game or have a save become corrupted.
Oblivion is just random like that.