2. Yes, from the perspective of the photon. I answered this first because the answer to the first one is much more complicated.
1. Photons having a rest mass of zero
is a consequence of the theory of relativity, or at least that's my understanding. It's apparently necessary in order to bring them in line with the rest of the theory of relativity, since even though photons can't be brought to rest so we can actually measure their mass, treating them as if they have no rest mass gives the correct equation for the energy contained in light.
As for why it doesn't experience the passage of time, that's because time (and time contraction) is a consequence of having mass. Clocks near to gravity wells run slower than ones further away, just as clocks on something moving at relativistic speeds run slower that something not moving at those relativistic speeds. That's why scientists treat the mass of an object that's moving faster as higher than the same object at a slower relativistic speed. In short, greater mass = slower time, and lesser mass = faster time. But for a photon, which apparently doesn't have mass at all, it also doesn't experience time at all.
Basically, the less mass something has, the faster time passes for it. Another way of putting this is that the interval between units of time is directly proportionate to its mass, so if mass is less than 1, the time interval between units of time also becomes less than 1. As mass approaches 0, the time interval also approaches 0. Since we have to set the mass of light equal to 0 in order for general relativity to explain the behavior of light, that means that the time interval that light has must also be equal to 0, meaning that there's no difference between T = 1, T = 2, or T = 1000000000000000. To the photon, they all happen at the exact same time, because there's no interval to keep T = 2 from running into T = 1 - or to keep T = 1000000000000000 from running into T = 1 or T = 2 for that matter.
You know, I'm beginning to wonder if this might not help explain the apparent expansion of the universe. If an increase in mass equates to a contraction of distance, then wouldn't a decrease in mass equate to a stretching of distance? If this is right, as things outside our frame of reference move away from us, their mass also decreases (as far as we're concerned), meaning that the apparent distance between us and them increases. It's like the opposite of the effect we get when we start moving at relativistic velocities towards another object - the distance between us and them contracts (which is why less time would show on the clock for someone traveling at relativistic velocities to reach Alpha Centauri than our clocks would show). So if we're moving at relativistic velocities away from another object, then presumably, the distance between us and them would expand.