The process is more difficult than the sales reps make it sound. In fact, you'll probably get some replies to your question suggesting entirely different ways to book, including trading your points privately, renting your points and using the cash to buy accomodations, owning another timeshare for this kind of trading and so forth.
To make this work, especially in a difficult-to-get location such as Maui, you should start at least a year ahead and give MS both a selection of resorts and a range of weeks. Then hold your breath for months and hope something comes up.
One location that usually does work is the Kona Coast on the Big Island. You'd still want to plan ahead, but it's so much more likely to score than the other choices that if you include it on your list, that's probably what will connect and where you'll go. Do remember that the Big Island is different in character from Maui: more volcanic, drier and less beachy. (My family prefers the Big Island for the adventure, but you might not.)