Two years ago we did a multiple island Hawaii trip - Oahu, Big Island, Maui. I planned everything myself and this is before we had a timeshare. I was able to find RT tickets from Denver to HNL for $342 pp. I signed up for a Travelocity Fare Watcher alert for DEN to HNL, and for it to email me when the price dropped below $500 (at the time, prices were running ~ $600). I signed up for this alert in October 05, with the intention of going in July 06. I constantly got emails from them, but summer dates were never available. Finally, in February 06 (5 months before our trip), Travelocity emailed me on a Sunday morning. When I checked the dates through their link, all of summer was wide open. I picked mid-July, and booked it. Later that afternoon, I came back just curious to see what was still available.....the summer was gone. It happens THAT fast. We did not use FF miles or anything. This was just being able to jump on an email from Travelocity literally right away.
BTW-with no time shares and no FF miles, we did Oahu, Big Island, Maui, 16 days in paradise, plane tix, activities, food, lodging, rental car, interisland airfare, souvenirs....out the door for $5000 for the 3 of us. I think I did pretty well.