In addition to when you go, there is another factor, which is how much bother is acceptable to you.
When people say "I got what I wanted using the waitlist" - that's great and they are happy. But going on the waitlist would drive me nuts.
When people say "I called day by day" - for some people that's acceptable (we did it for our next trip needing something special). For other people, having to get up when MS opens (particularly if you are on the West Coast) and make a phone call every morning is not acceptable to get what you want.
For some people it simply isn't acceptable to have to plan at all. We've had members post who were irate that what they wanted wasn't available to them four months out.
Some people are flexible. When the standard view at Boardwalk they hoped for isn't available at seven months, they are delighted that preferred view is. When they get two days on their waitlist for BCV, they don't see the lemons of having a mid-trip move, they see the lemonade of getting a few days worth of StormAlong Bay. Some people go on the waitlist for the resort they want, but are happy to stay at the resort they booked if it doesn't come through. Other people are less flexible and expect the system to meet their needs more precisely. They see having to spend more points, they see having to move mid trip, they are disappointed to the point of letting it affect their trip when they don't stay where they want.
Only you know what kind of person you are. But I think its important to be honest with yourself. If you will be "excessively disappointed" not to get a Boardwalk Villas standard view room over F&W, you better own there. If you can honestly say "hey, we'd be happy at our home resort" then it doesn't really matter where you buy.
When people say "I got what I wanted using the waitlist" - that's great and they are happy. But going on the waitlist would drive me nuts.
When people say "I called day by day" - for some people that's acceptable (we did it for our next trip needing something special). For other people, having to get up when MS opens (particularly if you are on the West Coast) and make a phone call every morning is not acceptable to get what you want.
For some people it simply isn't acceptable to have to plan at all. We've had members post who were irate that what they wanted wasn't available to them four months out.
Some people are flexible. When the standard view at Boardwalk they hoped for isn't available at seven months, they are delighted that preferred view is. When they get two days on their waitlist for BCV, they don't see the lemons of having a mid-trip move, they see the lemonade of getting a few days worth of StormAlong Bay. Some people go on the waitlist for the resort they want, but are happy to stay at the resort they booked if it doesn't come through. Other people are less flexible and expect the system to meet their needs more precisely. They see having to spend more points, they see having to move mid trip, they are disappointed to the point of letting it affect their trip when they don't stay where they want.
Only you know what kind of person you are. But I think its important to be honest with yourself. If you will be "excessively disappointed" not to get a Boardwalk Villas standard view room over F&W, you better own there. If you can honestly say "hey, we'd be happy at our home resort" then it doesn't really matter where you buy.