What if we give the falling observer and the object-before-it a propulsion system that would exactly counteract the gravity acceleration at any moment of falling down? That would make them stationary.
If they're stationary, then they're not in-falling, no?
They can still move at a constant speed relative to the black hole and be considered a "stationary observer".
Il Pal, it seems you do have a better grasp than you think! Sergarr, if you fire the propulsion system on both objects while they're both outside, nothing strange happens. If you fire them while one is inside, and one is outside, then you encounter the exact same situation as before; once the object is inside, it CANNOT come to rest with respect to you, since it would need to travel faster than the speed of light. If you were falling in after the object, you'd see it falling in too, along with anything else that's falling in.
The most intuitive way I've found of thinking about this stuff is with
Kruskal–Szekeres coordinates where any objects falling in use the regular T and X axes, and where any stationary observers use r and (little) t, in the number I quadrant. little r = 1 would be 1 unit away from the Schwarzschild radius. To better understand the I quadrant, stare at left half of this
Penrose diagram...
Another thing that really helped is this youtube playlist:
Topics in String Theory; lectures by Leonard Susskind. Lectures 3, 4, and 5, and maybe others deal with black holes a great deal, and really don't have that much to do with strings or quantum mechanics.
EDIT: Actually this video is basically exactly what we're talking about, with the 2 in-falling observers being explained at 1hr 0 min:
General Relativity Lecture 7 It's funny we were talking about it then I decided to keep watching this one, and here it is