Waitlisting is always a risk. If you had grabbed nights that were available, there is a risk the others would never have opened-up.
The
DVC reservation system will only match a wait list request if ALL of your days open-up simultaneously. It does not hold days waiting for more to be freed-up. Unless there is a 100% match, the available days will remain available for other guests to book.
Success usually hinges on specifics. If your trip is 7 months away and you're trying to get 2 or 3 nights in a large resort, you have a high likelihood of success.
But if you're a month away and you hope to get a full week in a small resort (or small room category / view), the odds are slim.
I would never book scattered nights in the middle of my trip. That's not a risk I'm personally willing to take.
But, if the trip is a long one and I find 2-3 days available at either the beginning or end of my stay, I might book those at another resort. Worst case would be a split-stay where I have to change resorts one time mid-trip. And it leaves you with fewer days to place on the wait list for the desired resort.
In 10 years we've used the wait list maybe 6 or 7 times and only once did we not get what was requested. It's not a perfect system but it works fairly well.