I'm a little unclear on your question, but if the award is for the same achievement multiple times, then you should simply say that you won that award eight times, on these dates, and leave it at that. You can add more detail about how what you did on one team was different from what you did on another team, but no need to repeat redundant details.
I would list your professional awards first, and list them chronologically, just like listing job experiences on a resume.
Questions 3 and 5 seem like the best fit for talking about your community service. Don't feel that you need to write about them in Question 2 just because that one mentions awards.
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