Bob would have a hard time seeing your image freeze due to the extreme doppler shift and diminishing photonic energy. You apparently slow down and fade away from Bob’s point of view.
Looking up as you go through the event horizon (given a black hole of the correct proportions such that the tidal forces are not so great that you’re squeezed to death at the e.h.), you would see the ‘outside world’ compress into a circle overhead (the light from outside does follow you in).
Looking ‘down’ or ‘forward’ into the black hole from the outside might reveal some Hawking radition (if you could detect it and if it exists), or, superheated particles emitting energy as they collide with one another on their descent. You couldn’t see past the e.h.
Once you past the e.h., looking down would reveal nothing (you’re actually not heading forward in space anymore as much as heading forward in time – thus the inescapability).
If you turned on a flashlight past the e.h., light would look like it was working normally – locally. If you kept track of the beam, it eventually gets distorted back into the ‘down’ direction you’re headed. If you measure the speed of light from your frame of reference, it travels at c. Of course, your frame of reference is severely distorted compared to those outside the e.h. In other words, your ‘straight edge’ is very non-euclidean and your ‘time’ is dilated.
As you approach the singularity, what you see of the outside is increasingly shrinking to a point overhead. Space and time gets more and more distorted. Gravitational tides rip you apart and you stop observing.
If you could survive at the singularity (which you can’t), know one knows what you would observe – all the formulas break down and give incomprehensible results at the singularity.
For more info, check out:
Now, what I want to know, which isn’t in the faq, is what you would ‘see’ when, as you pass the e.h., you look ‘sideways’ (i.e., perpendicularly) into the e.h. What whould that look like?