My guitar teacher gave me this piece to learn for my audition at Berklee, he said they love it everytime.

I have 2 years to learn it.

I don't really know what I'm trying to ask here.
How should I go about tackling this song?
What do you think?
Get a Aebersold play-a-long book of it. Go to jazzbooks.com and they have a whole list of books you can use to approach, play, and solo over jazz standards like that. They usually cost about $20, but if you want to get into berklee, that's a small price to pay.
Some of the most powerful moments are when there is nothing to be said
Well that doesn't sound too hard, especially not since you've got 2 damn years to do it.
Wise Man Says: The guitar is obviously female, she's got hips, breasts... and a hole.
UG's Flamenco Club
2nding the Jamey Abersold, and adding transcription. Lots of transcription. Listen to as many versions of it as you can, transcribe the one you like best, and then work out how they are getting through it. Do that a few times for different people and you'll have heaps of ways of getting through it. Proceed to mix, match, mash, expand and experiment.

Make sure you learn the form and head first, though.
How may The National D help you waste your time?