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Doctor's Orders gives you 4 extra loot midget spawns, which is why people tell you to never complete it if you're looking for Jimmy Jenkins.
If you did complete it, My suggestion would be to take Gibbed, and unflag the quest so you can just go do it again.
Make a BACK UP before you edit your saves though.
Open the chest and Hyperion ammo boxes to the left as you enter. Rinse and repeat. JJ will show up reasonably quickly but as with anything experiences will vary. JJ could show up the first time you do it or it could take a good few times. Luck of the draw.
This one worked - took my 70 minutes of constants saves and quits but eventually i got it :D