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There are various options that let you make your enemy drop a held object.
For example the "Disarm"-Action Option from the DMG or the "Disarming Attack"-Maneuver from the Battle Master subclass.
Would I be able to pick up said dropped object from the feet of the target as my "free" object interaction?
RAI, yes
Jeremy Crawford has this to say on the subject:
This might seem strange at first glance. Let's go back to the rules:
Moving Around Other Creatures
You can move through a nonhostile creature’s space. In contrast, you can move through a hostile creature’s space only if the creature is at least two sizes larger or smaller than you. Remember that another creature’s space is difficult terrain for you.
Whether a creature is a friend or an enemy, you can’t willingly end your move in its space.
The rules forbid moving through or ending your move in a hostile creature's space. You could interpret this to mean you can't invade a hostile creature's space at all. However, making an unarmed strike, as well as the Grapple and Shove attack options, necessarily requires invading their space and doesn't count as moving. It seems Crawford is treating picking up an item in the enemy's space the same way.
As one additional data point that this is probably the intent, Disarming Attack would be almost completely pointless if this weren't allowed. The enemy could simply pick up their item as their one object interaction on their following turn. It would take at least two creatures working in concert to deny the enemy his item - one to disarm and one to move the enemy - and both must succeed within the same round. You could attempt this multiple times with the Disarm rule in the DMG, but that's an optional rule.
Granted, Disarming Attack can provide some protection against opportunity attacks, but Goading Attack, Trip Attack and Maneuvering Attack do that job just as well or better.
No.
The Disarm action states that the item is dropped, without specifics as to where.
The Battle Master Maneuver, "Disarming Strike" specifies "The object lands at its feet".
The "free interaction with an object" assumes that the item is almost effortless to interact with.
Attempting to pick up something from an enemy-guarded space would require either an action to attempt to grab it from under their feet, or to force them out of the space (eg, Shove, PHB 195) so you can move into it. Once you have control over the space, then yes, it is quite reasonable to use your free interaction to pick the item up, if it is not unusually cumbersome in some way.
Probably not.
Picking up a dropped weapon is one of the examples given of interacting with objects on p. 190 of the PHB ("Pick up a dropped axe").
However, it's implied that a character can't interact with objects that they can't reach, and disarming attack causes the held object to be dropped at the feet of the targeted creature — that is (assuming both creatures are medium-sized), about five feet from the feet of the attacking creature. That's a long way to quickly reach down and grab something while a hostile creature is right there.
A DM might reasonably rule that the free object interaction doesn't extend to picking up or moving objects in other creatures' spaces. A better strategy would be to drive the disarmed creature away from its weapon, with a shove or a pushing attack.
