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.
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.
You do not need to be able to see the Mage Hand to be able to use it, otherwise ATs wouldn't be able to make the hand go invisible. However, working around corners (or otherwise out of sight) would effectively impart the blinded condition to any action you were going for. As such, you wouldn't be able to interact with a target except by guessing which location it was in (unless you knew the target's location, and it was static (i.e. an unmoving object (keys hanging on an post) or a guard that's asleep in a chair)).
Nothing about the spell itself implies any sensory input gained from the hand, so unless you can see what's going on to direct it, it's going to be pretty difficult to use. As a caveat to that, however: ATs can make the hand go invisible... therefore, they have to be able to at least "feel" where it's at.
If the door was simply a one-way door that didn't actually require a key, I'd say (unless you rule that the handle requires more than 10 lbs of pressure to activate) that it would work if she could get the hand into the room.
If she was suggesting picking the lock, I would say that's not possible because she couldn't get her mage hand or lockpicks to the other side of the door... unless she casts/pushes them through the keyhole/under the door (your ruling on whether the keyhole goes all the way through (in which case, she could pick it from her end)).
RAW: With an invisible mage hand, you can do the following (AT, Mage Hand Legerdemain, PHB p. 98)
- You can stow one object the hand is holding in a container worn or
carried by another creature.
- You can retrieve an object in a container worn or carried by
- You can use thieves' tools to pick locks and disarm traps at range.
In the spell text, it doesn't put any restriction on "any object not worn or carried," so it could definitely be used to take a crossbow bolt, or even pull the trigger prematurely.
RAI: You couldn't possibly see what you're doing with a fine lock or trap at range, so being blinded isn't an issue, because you can "feel" it through the hand. And you don't need to be able to see the hand. If she could get the tools, she could open the door from the other side.
As far as harassing people... that's pretty broad. You could apply 10 pounds of effort in quite a few fashions. Steal a handful of their arrows (and hold them up in the air (no more than 30 feet away from you)), undo their belt, tie their shoes together (or any other myriad wardrobe malfunctions), pull their hair or flick their ears(no damage), put a thumbs-up in their chair as they're about to sit down, use scissors to snip a cross/bow string (cruel, if it's a magic item - maybe only against mundane strings)... the list goes on.
This is situational.
I don't do two separate rolls, when it's a standard pickpocket or reverse pickpocket situation, IF the initial Sleight of hand is a success, but that's a DM call, as it is written.
So for instance, you want to reverse pickpocket a letter into someone's pocket. First, I have you roll to see if they notice--Dexterity (Sleight of Hand) check contested by the creature’s Wisdom (Perception) check.. If they don't notice and the sleight of hand is a success, I assume it's a success as far as it being carried out. (This makes sense to me because if it goes smoothly it won't be noticed.)
But if they DO notice, I THEN have the player roll to see if they got the job done anyway. So, you're picking their pocket, they notice, but you manage to get the wallet just as they notice. That would be Dexterity (Sleight of Hand) check, difficulty determined by DM, not contested by the victim. The victim might later be able to get it back or something but that's a whole different set of rolls.
If you're reverse pickpocketing, say, a damning letter onto their person, they can notice, but it might get in a pocket anyway. Of course, afterwards they'll take it out. But they might still have it in their hands at the right time. If it's some kind of magical incendiary they may have time to toss it away before it goes off. (They would roll for that themselves separately).
The exception to this rule, is if I am building suspense and it's particularly difficult--like line of sight is coming in and out because of a crowd of something. In those cases, the subject might not notice, but it's still possible to fail, and for the player to try again. In this case, I reverse the order of the rolls--first they roll for successfully pick pocketing, and then I have them roll the sleight of hand. It builds suspense, because the player can fail to pickpocket, but the subject still might be unaware, and the player can try multiple times.
With picking a lock at a distance, going unnoticed is totally separate from a success or not, depending on how close the noticer is to the lock.
The distance of the person noticing from the lock, determines whether them noticing would have any impact on success. So, if the person noticing the lockpicking is less than 5 feet away, I have them roll for the sleight of hand, and that might stop the attempt--basically, I handle it like pickpocketing.
But, if the guards are more than 5 feet away, I do both rolls at the same time, the sleight of hand, and the roll to pick the lock. Both are done at the same time, and while the person noticing might react, they are unlikely to prevent the success or failure of the person trying. Generally I give the player two dice, and assign different colors to the different things, and they roll them simultaneously. That's just DM flair.
Ultimately, it's up to the DM to decide what's fair, but this is how I handle these. Technically, and I do think you want to be technical here, there are supposed to be two rolls. One to see if you are noticed, and one to see if you are successful. I just handle it situationally, the better not to waste time on things, or the better to build suspense.