I did a long set of calculations exploring various scenarios for lowering things through a horizon. These calculations use a Rindler Horizon, but that works as a good approximation to the horizon of a black hole large enough that tidal effects are irrelevant.
It’s not exhaustive, but it’s nice to have some explicit calculations that are near enough to a few of the “Yes, but what if I did X?” questions that people sometimes propose as ways to “cheat” an event horizon.
https://www.gregegan.net/SCIENCE/Rindler/RindlerHorizon.html