No, the first two points don't hold for any caster with Mage Hand.
Pickpocketing isn't just taking something from a pocket; it's a subtle skill which requires doing so unnoticed, after all. This is more than just "doing it while the victim's back is turned" - the human body registers slight touches and subtle sensations, like the weight of an object. A pickpocket knows how to beat these senses - by touching the victim in other places to confuse the senses, for example.
But the Mage Hand is implied to be clumsy, with limited dexterity - not conducive to stealth.
(Note that nothing in the Mage Hand description says that the hand has significant dexterity - it can "open an unlocked door", for example, or "pour the contents out of a vial", but apparently not manipulate lockpicks or disarm traps, which requires more precision. It's limited almost exactly to simple tasks that you don't have to practice.)
So it's not that the Mage Hand eliminates the normal skill check as such - instead, the rules as written do not contain a "normal" skill check for picking a pocket with a Mage Hand. (A standard thief can't pick locks with a Mage Hand either, even if they somehow have one.)
Most people can undo the buckle on a bag, or shoe. But can you do so so swiftly and subtly that the holder of the bag (or wearer of the shoe) doesn't even notice? Try it. It's not as easy as it sounds. It needs significantly more manual dexterity than just being able to undo a buckle - it's more like being able to play a piano.
Under the old-school skill system of 3e or 4e, the correct way to handle this would have been with a skill roll and an extremely hard DC - as GM, personally I'd have set the DC 10 or even 20 points higher than the usual for that kind of pickpocketing. The old skill system would then have allowed top-level characters to pull it off anyway.
But 5e discourages this "everything is technically possible with the right roll" approach, in favour of limiting skills to "actions anyone could attempt". "Pick a pocket with a magical force" isn't something anyone could attempt, and there's no obvious RAW reason why being able to pick pockets by the normal means would help you use a Mage Hand to do so.
(And it is typically next to impossible to pickpocket successfully with a fully visible, somewhat clumsy, disembodied hand. So even a disadvantage is not enough penalty - it should just be impossible.)
Legerdemain clearly gives the hand more dexterity, not just invisibility. This allows for more complex tasks.
Short answer
If the standard hand doesn't have enough manual dexterity to pick locks or disarm traps, it doesn't have enough for the equally tricky task of picking pockets.
No...
...because being carried is not flying in the real world, nor is it in D&D.
That said...
...Flying is a type of movement in D&D, and movement is a non-action. Manipulating something with mage hand requires an action.
Plus, according to the text mage hand can interact with objects, not creatures.
You can use your action to control the hand. You can use the hand to manipulate an object, open an unlocked door or container, stow or retrieve an item from an open container, or pour the contents out of a vial. You can move the hand up to 30 feet each time you use it.
The Arcane Trickster Rogue's Mage Hand Legerdemain specifically grants the ability to interact with objects in the possession of another creature at 3rd level. This is clear indication that the general case for using mage hand does not allow it to interact with objects in the possession of another creature.
It isn't until ten levels later (13th) that an Arcane Trickster can directly interact with a creature, and only enough to be distracting. This specific ability is further evidence that the general mage hand cannot interact directly with creatures.
Best Answer
Mage Hand cannot do this
There are no rules that allow things to be dropped to deal damage. A GM may allow it (and this question reveals the lack of rules for this situation while this question discusses how non damaging a small object like a pebble would likely be.), but you would not use the modifiers from the spell because:
Not only is the mage hand not "someone else" (it's a spell effect), dropping it doesn't qualify and mage hand is unable to make attacks...
Even dropping the rocks should be considered an attack which makes it impossible for a mage hand to accomplish.
If your GM does allow it, it will be up to them what modifiers to use.