Definitely go on the wait list. We go through this every year with our family. My daughter's in-laws own a summer week at the Surf Club. We all plan to go together taking two 2 bedrooms Villas in July each year. They usually book their's as soon as we get back from our trip. Once they have the date booked for their owned week, we put in a request for the same dates, same view etc. using our DC points (we don't own an Aruba week). Usually within a month (11-12 months out per Dean's note above) our request is fulfilled and we have our units/ week set for next year's family trip. Once we arrive, we always are assigned villas on the same floor (usually right next door to each other). This works out very well and you should be able to get almost any week you want to book for (other than high demand holiday times). Good luck.
