We initially bought OKW in 2006. And we have used those points for every east coast DVC resort except VGF. We haven't had too much trouble. Yes, certain times of the year have been difficult (ie: F&W- we booked at 5 months out last year, got SSR but wait listed and got BLT 2 weeks later). You might have to tweak dates sometimes or take second choice. We had been trying to get BCV and finally got it in Jan 2013...probably because it's cooler and the SAB is a big draw there so folks want it when it's warmer (but it worked fine for us). You'll get to know the DVC calendar and the varying busy times at each resort and work around that. I booked an Aug trip (coming up) for my DDs and I at 6 months out and was able to get a BWV standard view studio with my OKW points (for 2 nights and SSR for the other 3 nights as each DD picked where they wanted and 1 wanted BWV and the other wanted SSR...worked out perfectly).
One piece of advice I like to give is to buy smaller contracts and multiple home resorts to maximize your 11 month home resort booking options. So, instead of starting with 250 SSR points...maybe start with 100 and then plan to add on once you know what resorts you want 11 month booking priority at. We started with 200 OKW and have regretted that, though we make good use of those (MIL and FIL use half of them each year and just LOVE OKW and staying in the HH section). We have since added and I have gone with resorts when we can conserve points (AKV- value and standard rooms, BWV- standard view rooms) but you do need that 11 month home resort priority to get those cheaper point costing rooms. HHI, we added because we plan to go there every other year so that we can save on park tickets and airfare and that was a place difficult to book during warmer months at the 7 month window. Now, though, with Disney giving us the PAP special pricing we found it's thrown our beach in even years and WDW in odd years plan out the window.
One piece of advice I like to give is to buy smaller contracts and multiple home resorts to maximize your 11 month home resort booking options. So, instead of starting with 250 SSR points...maybe start with 100 and then plan to add on once you know what resorts you want 11 month booking priority at. We started with 200 OKW and have regretted that, though we make good use of those (MIL and FIL use half of them each year and just LOVE OKW and staying in the HH section). We have since added and I have gone with resorts when we can conserve points (AKV- value and standard rooms, BWV- standard view rooms) but you do need that 11 month home resort priority to get those cheaper point costing rooms. HHI, we added because we plan to go there every other year so that we can save on park tickets and airfare and that was a place difficult to book during warmer months at the 7 month window. Now, though, with Disney giving us the PAP special pricing we found it's thrown our beach in even years and WDW in odd years plan out the window.