For those not playing on PC and don't use console commands.

• Sometimes it can be very easy, sometimes very hard to pickpocket ammo. The easy way to do it if you keep failing to pickpocket someone is to reverse-pickpocket one round of the same ammo type INTO the person, then you'll have a 100% chance of pickpocketing the whole ammo from that person.
• Sometimes you want a weapon the NPC is carrying but don't want to kill the NPC for it, and the weapon is hard to pickpocket even if you take all his ammo. What you need to do is shoot the weapon once (in VATS or so) with a high powered weapon, then holster your weapon away before the NPC becomes hostile. If the weapon is at 0% condition, the NPC will eventually unequip it when you leave the area and when you come back you have a 100% of pickpocketing the broken weapon from him.
• Want to give an NPC a grenade without killing him? Reverse-pickpocket any grenade into him (it'll go live), then quickly reverse-pickpocket any grenade you want him to have, then quickly leave the area before it explodes (a door works, or maybe even fast travel can work). When you come back, he'll have the grenades in his inventory and still be alive.

Pickpocket relies heavily on the sneak skill, and there are a few really nice to have sets of armor that boost a high sneak value even further.

Any time I get my hands on a Stealth Boy it goes into storage so I don't waste it on something that doesn't matter, there are much better ways to evade combat.

The La Phantoma magazines should never be wasted either.

Armors make you heavier and more noticeable, but you can unequip them if necessary or equip something that helps.

I think carrying a lot of stuff does the same, so go in light.

I'm not sure exactly what perks are helpful, never studied it out in detail.

Even if your Pickpocket skill is at 100, when you pickpocket too much it starts getting hard to pickpocket for a while.

There is a more easy way.

Steal the ammo and place a knife or something. go away, pass trhough a load screen (door) and come back. Without ammo, the NPC equipe the knife.

Well the thing is the chance of pickpocketing the weapon is easier the lower its value. If the weapon is completely broken at 0 value, the chance to pickpocket it is 100%.

Which is a great point: Percent chance to steal is in proportion to relative value, got it.

But you have to really want a thing AND have weapon repair kits to swipe a totally busted item.

Then again, to use a weapon repair kit you have to equip the item, and you can't equip something that is broken - so it has to be not quite broke OR you need to steal more than one OR you have to have the perk to fix it with a related item. Which is do-able.

Sometimes it's just easier and simpler to kill whoever has it.

I like Yan L's solution to making it available to pickpocket in the first place.

THIS I WILL NOTE (and some may call it cheating):

Unless you have ZERO% chance of stealing an item, you can save just before the attempt, try to get it, and if you fail reload the save.

*Save-Load tactics*

The law of averages means that sooner or later YOU WILL be successful, and then you save again.

Most mechanic abusing ways seem cheap though. Best legit way, and sme what difficult, is t get them to go hostile, hit it out of their hands & use sme turbo. You can pick up the weapon & run off. (Holster to stop combat as you can only hit them twice for this to work.)

If that does not work them C4 + detnater from a distance with a stealth boy. No rep. damage and usually everyone is non-hostile. Don't even ahve to pick the pocket as you can set it while they sleep.

"BAD MUGGY! No coffee cup..."

* To get Benny's gun Maria away from him, I had to use vats to shoot it out of his hands and try to grab it before he did.

(This was one of the challenges: "Talk About Owned" where you have to kill Benny with his own gun)

I didn't think about using TURBO - but yeah, you're right

* You have to wait until he is re-loading to shoot it

Benny is quick. You have to be right there on top of it to get this challenge to work.

You also CAN'T LET HIM RUN AWAY.

If he escapes, the next time you see him will be at Caesars fort

You will also fail the challenge if you set frag mines at the elevator he runs to...

The challenges are found under the "MISC" page of the "DATA" Pip Boy screen

You should check them out - they are pretty cool!

Last note on Benny, it takes a seriously high sneak skill to pickpocket the guy.

Get too close and he sees you, then a dialogue opens and the gun fight begins.

With jury rigging you can repair something at 0 condition with any similar cheap weapon.