A couple of weeks ago I built a plane with a drop pod to explore and get ground sample in specific Kerbin areas without having to land the plane (I would like to say because of rough terrains, but truth is, I'm a much better rocket pilot than plane pilot).
When trying to drop the pod, it disappeared (with Valentina inside) when my airplane was around 2.2 - 2.3 km from the pod. And when I said "disappeared", I mean "vanished into the void", it was not visible when I turned back or in the control station, not a debris, nothing... I guess Valentina ended up giving company to the kraken.
I tried to submit a bug report but apparently this is a known limitation that already existed in KSP1 (I never tried anything like this in the first game, so it was new to me ^^).
Of course, you can either drop from a very low altitude to avoid this, or manage to circle around the drop pod until it touches ground while being careful to avoid going over the threshold (which, in my opinion, would be a lot more difficult with a bigger aircraft).
I would suggest two things :
Find a way to communicate / alert the player that this limitation exists (at least through an in game alert) so you understand what happened and how to avoid it.
Increase the range, if possible, so that you have more leeway both in drop altitude and in circling range (to allow for bigger drops and bigger planes) ; and maybe make it a slider in the game options if it is too compute intensive on lower end configurations.
Note that it would probably not be needed as much in multiplayer as I imagine each player could occupy one of the two vehicles and then each would have is own physic "bubble".