I agree somewhat that you should get a contract where you want to stay, BUT.....in almost 4 years and 7 trips on points, we have only stayed at our home resort 1 time.
We are 5-2 month out bookers. Meaning we are flexible. 3 x boardwalk (1br), 1 x contemp tower (2br), 1 x poly (studio), 1 x riviera (studio), 1 x Copper creek (1 bedroom home).
i will say the only time we could actually get into our home resort was at 11 months. It is always full when we look less then 6 month out.
Flexible is key. If you are someone who wants what you want when you want it - "I promised my kids we'd stay at the Beach Club this trip, and the trip needs to be in October, and it must be a studio, and we don't own Beach Club" - you will be disappointed. If you are willing to take what's available, maybe a bigger room than you need, maybe move resorts during your stay, maybe move your vacation by a week or two.....you will be much happier (although you can still end up with no room anywhere booking two months out).
Generally, bigger resorts will be available longer. One bedrooms are the last to go. Near park resorts will fill faster. Value room options are seldom available at seven months. The last three months of the year (plus the first two weeks in January) tends to reach capacity soonest.