Yes, GI Bill will cover all flight training expenses, FAA written tests, and examiner fees. You'll also get a book stipend to help purchase academic books in pursuit of the AAS degree. Headsets, flight gear, and miscellaneous stuff is on you, but often you can get a college discount.
Yes, you can earn all ratings up to CFII/MEI in both airplane and helicopter.
Give the program director, and VA rep at COCC a call as the starting point. It's a close nit student body group, and you'll end up knowing a lot of your peers. There are a lot of vets in the program, from all services.
Bend is an awesome place to live and fly. I'd like to be able to move back there some day. The program and town are a hidden jem.