where you buy a Macbook/ Macbook Pro and get a free iPod nano or money towards an iPod.
It actually isn't just restricted to notebooks. iMacs and Mac Pros qualify as well (though most college students opt for the macbook for obvious reasons).
I was wondering A.) if it will happen again this year and
It seems to be an ongoing "tradition" so I think it will most likely happen.
B.) Begin with the release of a new Apple update or product?
Not necessarily. Last year the macbook pros saw an update with the sale's beginning, but that doesn't mean that it will always happen that way. The macbooks and macbook pros might see updates before the sale begins.
How much do you get off of an iPod?
It depends on which model Apple chooses to focus on that year. For example, last year it was based off of the 4GB nano (5 colors) so the rebate was for $200. In years past, it has been $150 as well, but again, it depends which model Apple is basing their "free" claim on.
Usually around mid-to-late June, ending sometime in September.
Although last year it did start early for some reason (June 5th).
OP, just stay tuned to MR and you'll know when it's starting on the very first day.
Yes, and it's $150 towards an iPod
On this point, I want to remind you OP that the rebate is only good for specific models of iPod. For example, the video nanos that came out last year were introduced while the sale was still ongoing. These nanos did
not qualify for the rebate.
In addition, iPods priced below the rebate amount don't qualify.
Good luck at university.

Where're you headed off to if you don't mind me asking?