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The darkness spell description says, in part (emphasis mine):
If the point you choose is on an object you are holding or one that isn't worn or carried, the darkness emanates from the object and moves with it. Completely covering the source of the darkness with an opaque object, such as a bowl or a helm, blocks the darkness.
Do you need to be carrying the item only the moment you cast the spell, or for the whole duration of it? Would the spell end if you're no longer carrying it?
Magical darkness spreads from a point you choose within range ...
If the point you choose is on an object you are holding or one that isn't being worn or carried ...
If the criteria for the point is met when the spell is cast then the darkness moves with the object, irrespective of how the objects is moved. If the criteria isn’t met then the darkness is immobile.
You don't need to be carrying the item at all, and indeed are not allowed to be carrying it unless you are actually holding it (e.g. you may not cast it on your hat, or belt buckle, or a dagger in a sheath).
You may cast it on an item you are holding in your hand, or you may cast it on an item that is not being worn or carried. In either of those cases, the spell is on that item and the Darkness persists thereafter.
The DM would have to rule on whether you may cast it on an item you are holding, and then wear or carry it. It would seem strange to me that you cannot cast it on your hat on your head, but could cast it on your hat in your hand and then put the hat on your head and it works. I would, accordingly, rule as a DM that the spell no longer moves with the item if the item is subsequently worn, or carried without being held.
So, to answer your question directly:
You may cast it on an item and leave it somewhere (or throw it, or kick it somewhere) and the Darkness will move with the object and stay where the object stays (as long as concentration is maintained on the spell, of course).
And indeed, I would say that you may cast it on an item and give it to another person, and the Darkness will persist, and travel with the item, as long as the item is held by the other person, and not worn or carried other than held in hand, and concentration is maintained by the original caster. That however, is not explicitly defined, and would be a DM ruling to decide.
If you cast it on an eligible item, and that item becomes no longer eligible (i.e. someone puts it on to wear, or hangs it from his belt, then the DM must decide what happens. He could (a) rule to let the spell persist on the now worn or carried item, (b) rule that the act decouples the item from the spell, and the spell persists, unmoving, at that location, or (c) rule that the act ends the spell on the no-longer-valid target. I would go with (b).
If the point you choose is on an object you are holding or one that isn't worn or carried, the darkness emanates from the object and moves with it.
Rules in 5e are worded very intentionally. The key operator here is OR. To be able to move with the objects it must satisfy as least one condition, i.e it must not be worn or carried OR it must be held (by you). Because of the OR operator if only one condition is met it still fills the criteria for moving with the object.
If the operator was AND both criteria would have to be met.
So what does this mean? Say your character is wearing an amulet it would be perfectly valid to hold the amulet whilst you cast the spell and fulfil the criteria for the darkness moving with the object. Similarly if you were to be holding onto you hat. Same would apply for an object you are holding that is worn by an enemy (seems a bit situational but could be part of a strategy).
Casting through a familiar is invalid as the spell is still a ranged spell and familiars may only cast your spells with a range of touch.
Lastly the criteria needs to be met at the time of casting. Whether it breaks if the criteria is no longer met is unclear but from a "realism" standpoint it wouldn't make sense for it to move with an object, then when it is worn the darkness just freezes in the space it was put on. A way to constantly satisfy the condition whilst in combat and still be able to fight would be to cast it on a held weapon but from my interpretation it should be able to move with the object once cast.
The spell says
or one that isn't worn or carried
This would include objects that you leave somewhere. You don't even have to touch the objects as long as they are in range. You just can't target an object someone else is carrying and you can't target any worn objects.
The darkness will only emanate from the object as long as the condition is met. Once someone puts it on or someone else carries it the spell will stop being tethered to the object.
In this case the point in space will stay stationary.
This is a consequence of the placement of the darkness emanation clause
If the point you choose [satisfies these conditions] the darkness emanates from the object and moves with it.
The point that serves as the center of the darkness must meet the criteria of the spell or the effect does not have that qualifier. It is a simple "if, then" statement.
