My first problem:
Often, when I try to tune to Drop D, I break my Low E string! Any way I can avoid this? Doubtful, but I'm still curious..

Also, I am learning a song with the tuning (Low to High) CACECE and I just needed to know if I would be tuning the certain strings that are changed up or down... thanks!
well you may need to wind your strigs around the post more times, and as for the other tuning, in most if not all cases tune to which one is closer

for CACECE im posotive you would tune....your low E down 2 steps, your A stays the same, your D down oe step, your your G down 1 and a half steps, your B up 1 step, and your high E stays the same
I'm not sure what to tell you on the string breaking...but as for tuning to CACECE...low E is dropped two whole steps to C, A stays the same, D is dropped a whole step to C, G is dropped a step in a half to E, B is raised half a step, and high E stays the same....Hope that helps
Your E string shouldn't break tuning down so I bet you're turning the tunning peg the wrong way. And the CACECE is
E tune down two steps
A stays the same
D tune down one step
G tune down a step and a half
B tune up a half step
E stays the same
Stock Gibson Pickups from a 2005 V, I think they're a 498T and 500T set FS/FT
Duncan Distortion (regular spaced) FS

Looking for: an acoustic, recording gear, or $