Hello Jimi:
My question is, does his observations of time dilation and length contraction, or any other observations/realizations he made, serve to explain just why and how light always moves at the speed of light?
As already answered, no, it's kind of a mystery.
And it is counterintuitive, seems like Einstein first thought about it around age 16...even took HIM a while to figure out...The greatest minds of the 1920's were flummoxed by time dilation and length contraction...[Lorentz and Fitzgerald couldn't quit figure it out, for example] searching for a 'luminiferous ether' as a possible explanation.
It took an Einstein to make a further step in understanding. It was his keen ability at physical insights rather than extrordinary mathematical ability that led him. That's why flat spacetime is called MINKOWSKI spacetime rather than EINSTEIN spacetime [LOL]; Minkowski was his former professor and it was Minkoswki who first realzed Einstein's new theory of special relativity should be reformulated in four dimensions...three space, one time.
It turns out that in our everyday low speed environment, space and time are mostly fixed and unchanging...time tick, ticks along at a steady pace, space remains fixed. It turns out that is true only locally, right where you stand, or move. As soon as you look further out with relatively high speeds between observer and observed, our everyday intuition fails: space and time are not what they appear. Lorentz transforms rule the day! Space and time 'conspire' so as to keep the speed of light constant.
One good 'rule' to remember: Your own clock, carried with you, always ticks at the same steady pace. Thats YOUR 'proper time'. And you own local ruler, right there with you, never 'changes length'. You can trust your local instruments accuracy! The other guy as a distant observer may see your clock tick differently than his, and your ruler different than his ruler, but you can be sure yours is fixed and accurate.
Also, it is helpful to know before you get into lots of details, which can get confusing,
that while SR shows us space and time are relative, GR tells us that in addition, changes in gravitational potential show further changes in the pace of time. So in a sense, SR weakens our everyday notions of fixed space and time and GR weakens those notions further.
PS: Another guru here plays guitar, if I recall, sophiecentaur...we recently had a discussion on the natural frequency of wood and electronic instuments...I'll send you a private message if I can find it.
edit: You should search 'guitar' in these forums yourself if interested...I did not realize there were so many prior discussions...