I wait list for my home resort a few times every other year, VGC studios, which are some of the hardest to get in the system since there are only 24 (23 if you take out the hearing impaired one, which I exclude now that I have that option which I'm very grateful for). They match a little more than half of the time, usually within a week of the 30 days. I don't stalk the site, don't have time for that.
I just had the 2nd to last week of June match, I had one night and was hoping to turn it into a 3 night stay, had waitlisted nights 2 & 3 together at 8 months, and listed just night 2 at around 5 months since I decided I wanted 2 nights or none. Got all 3 nights this time.
I haven't gotten a notification that my waitlist has matched in recent memory, has been a pleasant surprise when I log into my account. Seems weird that a new reservation doesn't trigger an e-mail notification.