Even though I don't own DVC, I read a lot about it on these boards, and I have a suggestion. Buy a direct contract for a fixed week. That way you wouldn't have to concern yourself with booking 5 months in advance as your week would be prebooked every year. Assuming you would want to travel the same week every year and can afford a direct-contract purchase, this could work out very well for you.
But for resale? I think you're playing with fire. It's the general opinion of everyone on the DVC boards that if you can't plan 11 months (even 7 is cutting it close these days) in advance, DVC is not for you.
ETA: I've given this a lot of thought since I often think of perhaps buying DVC, and this is the conclusion I've come to for myself--that if I ever bought, I'd get a fixed week so I wouldn't have to concern myself with trying to get the exact reservation I wanted.