Suppose an object falls into a black hole that's so massive that it wouldn't get torn apart at the event horizon.
What happens to it after the black hole evaporates away?
According to the theory of general relativity without Hawking radiation, from observers outside a black hole, it takes an infinite amount of time for it to reach the event horizon but from the point of view of the object falling into the black hole, it passes the event horizon in a finite amount of time.
The hypothesis doesn't make much sense. The resistance of an object to being ripped apart is given by its elasticity, not by how much is massive.
Anyway, to the central question there is no answer yet. This is the so called information loss paradox, one of the greatest unsolved problem in theoretical physics.
In general relativity the object falls in a finite amount of proper time and hit a singularity (assuming the most simple black hole, Schwarzschild). Due to Hawking radiation the hole evaporates completely and information is lost because a pure state has evolved into a mixed state.
One of the most promising resolutions to the paradox is given by string theory: the fuzzball proposal. Basically the hole is a sort of very degenerate stringy star (there is an over-over simplification here) free of horizon and singularites that radiates more like an usual piece of burning coal, so the information is not lost. The crucial point is that (in the usual simplified picture of pair particles produced near the horizon) the place in which the particle are produced is NOT vacuum, so the there is not information paradox in the first place.
from observers outside a black hole, it takes an infinite amount of time for it to reach the event horizon
Turn on your logic. If the black hole evaporates in finite time, it will evaporate before the faraway observer will see the infalling observer reaching the horizon. So, after the final evaporation event the faraway observer can meet the infalling observer and ask how he feels.
