What to look for when purchasing a headset I'm currently a student pilot, and I'm starting at an aviation university this fall to major in commercial aviation. Needless to say, I will be flying a lot. I'm looking to upgrade to a nice headset from the pretty basic one I have now, and I'm looking for a bit of guidance. I'm 6'3, so I wouldn't say I have a small head, and I've had problems in the past with headphones feeling cramped on my ears, which I don't want to be the case with my headset. I plan on having this headset for a while, at least all the way through college and hopefully several years after that.

First of all, is noice-cancelling actually that important(in terms of health and comfort)? I know there are a few decent headsets are out there w/o noice cancelling, and they are quite a bit cheaper than noice cancelling headsets.

I've been told about a couple commonly used expensive headsets that are pretty widely used across the industry. However, these headsets are $850+. At this price level, does the price of the headset accurately reflect quality, or is everything more personal preference? What are some of the pros and cons of the more popular headsets, and what should I look for when purchasing one?
I've had problems in the past with headphones feeling cramped on my
  ears, which I don't want to be the case with my headset


Do your best to test them out before you buy. Some pilot shops will let you put them on your head and if you are nice to the people that lurk around the airport they may lend you one for a flight to try out. I find that the Zulu's have bigger ear cups than the Bose but I don't have any hard numbers on size this is personal experience wearing them. 


  First of all, is noice-cancelling actually that important(in terms of
  health and comfort)


Yes, just ask any one that flew in the pre-headset days. I personally find that I can comfortably fly for longer times with an ANR headset. Another thing to note is that the ANR head sets tend to not squeeze your head quite like the passive headsets I find this to be the real gain in comfort. 

One of the big functional differences is that some of the LightSpeed headsets do not cary a TSO, I belive all of the Bose do. This may impact your ability to use them for commercial purposes in the future. You can find a discussion on it here.