DJR, I had a very long reply typed out covering your question as pertains to my experience with Marine Corps WO's and some Army WO's. I'll spare you the long reading and me the long retyping.

Yes, WO's can and often do possess degrees. It would probably be more rare to find a WO that -didn't- pursue some kind of higher learning. They are normally the type of people who will pursue degrees just for the sake of expanding their knowledge on a given subject.

If you want to fly helo's then apply for the Army's WO Rotary wing aviation positions. If you want to be an officer -and- fly helo's then join the Marine Corps or Air Force, but I would suggest the Marine Corps. Not just because I am one but because we have more options when it comes to the type of aircraft you can fly. Some flyboy can correct me if I'm wrong but I think the AF is limited to the Pavelow and I'm not sure if they have Blackhawks or not. In the Marines we have CH-53 Super Stallions (Pretty much a base model Pavelow with no ECM), UH-1N Hueys (Or Iroquois if you must), AH-1W Super Cobras, and CH-46 Sea Knights (Don't ever get on one if it ain't leaking something). Not to mention you could always fly jets, Hercs, or even Harriers