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I apologize if this has been asked. But, I have not been able to find an answer.
Assuming an acso completes their first contract of 9 years. What happens after if they choose to extend? Does the cycle repeat itself?
1st tour operational flying post
2nd tour instructional at Winnipeg
3rd staff position.
Or do they tend to stay in a staffing position for the remainder of their career?
First, the instructional tour isn't always in Winnipeg - it is more likely to be at the Operational Training Unit for the airframe. After that, it's less structured; some will be Majors and go back for a Flying Supervisor tour at a squadron, some will stay as staff officers, etc.
The staff position (#3 on your list) isn't guaranteed either - some people have never done a staff tour in 25+ years of service. It all depends on what the need is and what your preferences are.