First, good luck!
Your best chances of getting a W/L are at one of the bigger resorts, and for shorter rather than longer periods of time..i.e., SSR, OKW or AKV--because they have so many more villas--are most likely to open up. And, one night or two nights are more likely than 3 or 4 or more...
But it's all "luck of the draw"...I've seen/experienced W/Ls come through for smaller resorts, too...
The rules limit you to two active W/Ls at a time, so that make SSR your best bet...there are no views or other booking categories to make your "pool" of possibilities smaller...at AKV, you have to pick between Jambo and Kidani, and several different categories from there (value, standard, savannah, concierge)...and since you can only have two W/Ls, the categories can matter...
Your points don't get used until/unless you W/L comes through...so there's no impact at all on your points unless the W/L comes through...
To maximize your odds, here are some "tricks" you can use:
1. You don't say for how long you wanted to book...if it's "just" a weekend or long weekend, I'd go with SSR, and then OKW (not near HH). If it's a week or so, I'd consider a split stay, and W/L'ing 3 days at one resort and 4 at another...
2. DO snag what you can get now (what's available)...also check the website frequently...openings (especially one or two days) pop up frequently and you may be able to get all (or most) of your dates "in pieces"...don't forget if you wind up with a night or two "missing," you can sometimes book that same room on cash (and then W/L it for points)...
3. Don't worry about turning multiple one or two night reservations into a a single (or just two) reservations just yet...wait til you think you're "done" and then call MS and have them link (e.g., if you get 2 nights at SSR today; another night in two days, and then another 2 nights next week, you can have all 3 of those separate reservations linked once you've "finished")...
Piecing together a reservation (especially this close to arrival, and during Food & Wine, which is a busy time for
DVC) can be done, but it takes persistence, some luck, and some knowledge of "the system." If you're ok w/staying at SSR, that's where your best chances are (because of the resort's size)...one bedrooms are easier to get (and twice as expensive!) as studios, so you may be able to get your dates in a one-bed if not in a studio...
Using the website will make it easier than having to call MS...but my best advice would be to book immediately each time you see one of your dates come available!
Good luck!
