This question has been bothering me for a while. I have a crude hypothesis...
As I understand it, an observer falling into a black hole will cross the event horizon at some specific future (proper) time in, and that it will not be a traumatic event if the black hole is big enough (e.g. tidal forces will be quite mild).
Also, an outside observer will never observe the infaller quite reach the event horizon but it does not work the other way. The infaller will not observe times arbitrarily far into the future before crossing the event horizon..
Also, black holes evaporate, which may lead to some caveats about the previous two statements (which do not take evaporation into account).
So suppose we have a large black hole, destined to evaporate and vanish in the the year 1050 AD. And suppose I jump into it, equipped with a telescope that lets me observe the Earth. Before I reach the event horizon I will see 1050 AD arrive on earth. At that point I will see astronomers on earth waving flags to indicate that they have seen the black hole vanish. So if I look "down" I will see empty space with no black hole looming. So where am I? If I'm just adrift in space, am I in a cloud of all the other objects that ever fell into the hole?
Now for my crude hypothesis: as I fall, and the hole gets smaller, and the curvature near the horizon gets more acute, I'll be racked by tidal forces and blasted by Hawking radiation. Any extended body I happen to have will be disintegrated, so "I" will survive only if I'm an indestructible point, and the cloud of such particles is what astronomers see as the final flash of Hawking radiation. Is this even close to plausible?