I wait listed for Disney's Vero Beach Resort last year and did so again this year.
In 2006, I got on the list in February for an end of July early August vacation. I had them book dates for a two bedroom automatically without calling me first. I did the wait list by days. I received some dates the very day I got on the list, some in March and my final two days in June.
I put my last two dates on "cash" reservations in May in case my point reservations did not fill.
DVC keeps a certain amount of space available for cash reservations. When my final dates were filled using points, I just canceled the cash reservations for those two nights. There was no penalty for doing this.
This year I am doing the same thing for the same week as last year. I made my reservations in February and had some days reserved the day of my initially calling. Two more nights came available a few weeks later. I am now waiting on my final two nights. If they do not fill by May, I will make cash reservations again, just in case. I will cancel the cash reservations if/when my remaining two days fill using points.
The reservations are all linked, so you're not going room to room during your trip. I believe the wait list automatically cancels 30 days out. Maybe someone can clarify this point if I am wrong. And you can call before they cancel and ask them to keep you on the wait list down to I believe 7 days before the trip.
Again, if you have a gap...make reservations for "cash" just in case. You can do this directly through DVC Member Services.
I personally think you have a better chance of getting your reservation filled doing it day by day as opposed to trying to get an entire week filled. But there are various opinions on this. Good luck!
