#1
Is there some sort of trick to tuning strings higher? I'm looking to learn some songs where the B might be up to a C or D, high E up to F or F#, etc.

I've tried but have broken so many strings I've just given up.

Any advice?
...because the last thing the world needs is another metal guitarist.

Me.

My band.

I like Fall Out Boy. I don't like you.
#3
If you get .009's the b string shouuld be .011 which should tune to anything under high e nicely. I am unsure about when you should stop for tuning up the high e though with .009's. If you throw in a .008 as your high e a point .011 as your b you should be able to tune to those notes quite easily.
#4
Hmmm... so thinner strings have more give, and can be tuned more taught?

I use 10-46 for electric and 11-47 for acoustic
...because the last thing the world needs is another metal guitarist.

Me.

My band.

I like Fall Out Boy. I don't like you.