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Do you prefer to be surrounded by other tourists with relatively clearly defined activities (Waikiki, Maui) or do you prefer it off the beaten path, surrounded by a more authentic local vibe but you're more on your own for entertainment and activities (other parts of Oahu, Kauai, Big Island)?
Are there any must do activities? Hiking, diving, musuems, Matsumoto shave ice, seeing how incredibly tiny the beach at Waikiki is, etc.
Weather in September should be fine with highs in the upper-80s and overnight lows around 70. Much in the way of serious rain would be pretty unusual but can vary by island and side of island.
How long are you planning to go? If you have a full week or so, and since it is your first time, I'd probably suggest starting on Oahu (but not Waikiki) for a few days and doing the standards (North Shore, Pearl Harbor, Hanauma Bay, etc.) and then hop over to one of the neighbor islands (Big Island or Kauai rather than Maui or Lanai) for a few more days to get the different flavors.
As for price, June to mid-September is the peak tourist season so if you're looking at early September you'll probably have some challenges finding discounts. But again that will vary by what kind of travel is your preference. A rental condo in Kaneohe will be vastly different thing from an all-inclusive on Lanai.
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