So lets assume I can see the clocks one approaching the speed of light and the other one approaching the event horizon. Both of the clocks will be running slower than the clock I am holding in my hand. My question is why does time change with two very different events? Do they have something in common that I'm just not understanding?
This could get close to one of the SR paradoxical thought experiments but...
Yes they do have something in common but it may get a little tricky trying to explain it.
In a way it is tied up in the equivalence principle, or an extrapolation of it.
The equivalence principle says that if you are in a box with no window you cannot tell whether the box is at rest on earth or under a constant acceleration of 1 g in empty space. To know which you have to look outside the box to see if you are moving.
The equivalence principal connects gravitation to inertia in that what you feel as gravity when you are accelerating is your inertial resistance to the constant change in motion due to the constant acceleration.
Moving at the speed of light your inertial resistance reaches infinity and you can go no faster.
At the event horizon, or the exact point where the escape velocity is c, any attempt to move away from the BH is met with an infinite inertial resistance just as if you were traveling at c. In fact to just sit there you would have to be accelerating at c away from the BH just to keep from falling into it.
Both situations are indistinguishable. You could not tell if you were in a box at an event horizon or in a box moving at c.
The paradoxical aspect is that some would tell you that if you were in a space ship moving at c you could not tell it. Or that if you were in a spaceship at the event horizon you could not tell that. Everything inside the spaceship would seem normal. This is a trick of time dilation that does not account for the inertial aspects of the two situations.
If you are in a ship moving at c, you could not walk from the back of the ship to the front of the ship without exceeding c. Actually you could not move from back to front because your inertial resistance to motion in that direction would already be infinite.
O.K. So you are at the event horizon again, this time you are in a stable orbit. Experience says that you would feel weightless. You would be in free fall, a point where the fictitious centrifugal force and the gravitational pull of the BH balance one another. But this does not quite work either, because any attempt to even raise a hand is a motion away from the BH and there is already an infinite inertial resistance to any motion away from the BH. (beside the orbital velocity at the event horizon is likely close to if not at the speed of light and that alone would result in an infinite inertial resistance to any further motion in that direction, as in the previous example.)
It really is a good thing that time stops in both cases because that way if you are the observer you never have to know you are trapped.
I hate these things... They get too convoluted and full of well what if this or what if thats.