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This also would be my guess. Having 3 items with stealing would give you 3 rolls on which item you steal and once you stole this enemy doesn't have anything left to steal. That you can steal more than 1 item however kinda surprises me. I rather thought it would increase the chance of stealing the more valuable items(which it still would do with 3 chances).
Matt's Stealing ability has no interaction with the stealing chance on equipment, but if you have 3 stealing boosting items then you have 3 chances even if you only see 1 of them being displayed. I once noticed how the bubble with the stolen item overlapped with another so I saw what I did steal first and then the 2nd or 3rd one for a part of a second. I did try it with 3 items boosting stealing ability and did steal with NoLegs Diamonds from an Viking Monolith even if it wasn't displayed, just attack, run and attack in next battle and check your crafting materials.