You'll only get the O-1E paygrade if you had at greater than 4 years of active duty enlisted (read 4 years + 1 day of active duty or 1461 points). If you were a traditional Guard or Reserve bum for those 8 years and have less that 1461 points, you'll won't get O-1E. As for flight pay, if you were an enlisted flyer (Loadmaster, Boomer, etc) your prior flight status doesn't count. You start over at 0 years for flight pay purposes.