Oh boy, so explaining without diagrams...haha let's see. I hope someone will correct me as I am also a layman but I thought a couple of your guys' questions here were really interesting, and also thought that I had some long shot at answering them properly. I basically read A LOT of my astronomy textbook when I took the class, and physics courses, so here goes...
Repertoire: Light does funny things! :P I might be wrong, but I think some of the apparent trouble exists because we tend to think about light in terms of particles when it does not behave entirely like a particle. If you were traveling at 100 m/s (in a vacuum thank god) and fired a gun with a muzzle velocity of 100 m/s, the projectile would be traveling 200 m/s with reference to the total stationary frame. So at c, as a limit, it seems intuitive that if you were traveling at .9c and turned on a flashlight, the beam must only be traveling .1c faster than you (It can't be measured at 1.9c from any reference frame anywhere). Unfortunately for our sanity, the light from your flashlight's speed is measured by you as 1c not as .1c, even though that is the amount its velocity exceeds yours. The stationary observer would record your speeds "correctly" at .9c and 1c, but you still observe the light's velocity to be 1c, and it would appear to race away from you at that velocity.
And why? Well, we're not sure. I don't think we know why this is the case. This is really tough for me to explain in writing and I'm not sure this is making sense, but it might help to realize too that the object in your scenario doesn't "know" that it is moving at whatever velocity it has. And even if the light particle B reached the object first, none of the individual particles would have exceeded c. In other words, the distance covered between it and particle B could exceed the distance that light can travel in that time, even though nothing went faster than the speed of light.
For example, say you have two particles A and B which are 2c apart (as a distance, the distance light travels in 2 seconds let's say). Each particle is moving at c (the speed of light). In one second the two particles will meet right in the middle. While it seems the 2c distance was traveled in just 1 second, neither particle exceeded c. An observer would see that the 2c distance had been closed in just 1 second, but that each particle moved towards each other at exactly c. Since particle A doesn't "know" that it's moving, even though it began the time 2c away from B, it observes B covering a distance of 2c/2, or half of the total initial distance between the particles, and it observes B covering this 2c/2=c in 1 second.
So even though the distance covered is greater than light could have traveled in that time, the particles are obsevered from any reference frame in the example to be traveling at no greater than c.
Chaslie: I believe that it is true, that in a situation where the velocities are already established (ie- no more acceleration), you cannot say whether you are approaching an object or the object is approaching you. In the case when you have experienced the acceleration, you would be able to judge. There's really no paradox. While it seems that because the twin is flying away, neither of them could tell which description of the event is "true", both brother's do not experience the same acceleration or same "events". The time dilation occurs in the one way because their experience of events is not similar, though at times they would be unable to tell in an instant what was happening, they started from the same reference frame. The brother who stays home never leaves that reference frame and experiences no relevant accelerations besides the normal Earth ones, while the twin in the rocket leaves their initial reference frame and experiences acceleration while he is leaving, and as he turns around. Though they "couldn't tell" in the sense you mean, anyone on the Earth would see the one brother accelarate to and fly away at that speed, swing around a star, and then come back.
The description of the events for both brothers as judged from the initial reference frame are different.
Supposedly (I found this interesting), due to gravitational time dilation, as a person is approaching the surface of a massive black hole, an observer from a sufficient distance from this, will see that time has slowed down for him, while the person near the black hole will see that time appears faster for everyone else. As the "astronaut" crosses the event horizon, time will appear to stop completely for him, while he will see the enternity of time in the universe pass in a blink, although time for him, as perceived by him, remains unchanged and he will otherwise pass through the event horizon as if nothing had happened (assuming he could survive being strectched). At which point he would never be heard from again... ^^
"Because, wouldn't the photons that are reflecting off of it take that much longer to reach you?"
Nope. And couldn't tell you why. They bounce off and would still apparently travel at the speed of light. Don't know why. "This stuff is just incredibly mind-boggling." True!
I also used to be of the understanding that time itself was slowed for the person moving at high speeds, but that's not actually the case. For them, time, and chemical and aging processes, etc., go on as normal. It's just that their high velocity relative to someone else's velocity makes their time "seem" different, relative to the other person. If someone were traveling at .99c, they still perceive and experience 15 minutes in exactly the same way, except that their 15 minutes was a different length of time in a different refernce frame. If that makes any sense -.-
Like, observering the fast moving moving person, you would conclude that they are moving in slow-motion, or that their brain function is slowed, but they would experience it just as you do sitting here, and if they could observe you, you would be moving in hyper time.
Now, I might be wrong about this, but two people moving at high speeds who never shared a reference frame, and are moving constant with relation to each other, can both see the other as being slowed down even though that seems like a contradiction, or that it would cause some sort of inconsistency in "actual" time, except that actual time apparently doesn't exist. I mean, if intelligent conciousness were not in the universe to perceive time, would it be a dimension? Wouldn't the universe come and go without any recognition or notion of time, without the passage of any events? Like it slept through the whole thing and nothing really happened...during all that ~time~? Just Kidding!
Anyways, I hope that answered some of the questions. Although Chaslie I didn't quite understand your second ones?