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What have you ruled as the DC modifiers for noticing a item being pickpocketed from different parts of the targets gear.

Here's the scenario that caused a lot of different opinions on the difficulty of the theft being performed.

Our second level party that consist of a monk, a paladin and a rogue, has just finished killing a seahag on the deck of a large ship, and the paladin of the party has found a small gem worth a 1000 gp from the body of the hag. The paladin drops the gem to his backpack and then continues to search the deck for more hags that could have climbed on to the deck of the ship.
The rogue of the party (that being me so I might be a bit biased here) is struck with greed and decides she wants the diamond for herself. As the paladin searches for the seahags with the "help" of the rogue. The rogue makes her move and does a sleight of hand check to get that precious diamond. Now the rogues throw is 19+9=28 for sleight of hand, and the paladins perception check is 14+8=22. Our DM ruled that the check succeeds and the rogue got the diamond, but this caused a lot of different opinions on should the check have succeeded.

Now the player of our paladin first suggested that there should be 5 sleight of hand checks vs. perception checks for the theft to succeed. Then it was lowered to 3 checks. One for getting the backpack open, one for digging for the diamond, and one for getting the diamond out unnoticed.

I personally don't favor multiple checks where one party only needs one success and the other has to succeed in every roll.

Later on the player of the monk suggested that the DC for stealing something from a backpack that is on someone’s pack should be as hard as or almost as hard as stealing a sword from someone’s belt.

DC 50
Task: Lift a sheathed weapon from another creature and hide it on the character’s person, if the weapon is no more than one size category larger than the character’s own size.
http://www.d20srd.org/srd/epic/skills.htm#sleightOfHand

So the player of the monk suggested that the DC for the diamond theft should have been DC 40.

What difficulties would you as DM's and players suggest for picking items with sleight of hand from different parts of targets gear?
And do you think the paladin would count as being distracted because he was looking out for the possible seahags?
I seem to be the only one who seems to think that stealing something from a backpack shouldn’t be next to impossible
I would really appreciate the input because this incident caused a discussion that will set precedent for later stealing attempts.

And as an additional question, how would you think a actual thief would go on about stealing something from a backpack that is on someone back. By cutting a hole in the bottom and hoping for the right item to drop out, or some other means that would make the theft seem plausible?

I think that if the rogue wasn't being so greedy, she would have waited for the paladin to go to sleep and then search trough his backpack, but there was the slight possibilitity that the paladin would have hidden it better in that time.

Thanks beforehand for your answers.