My friends and I usually make a reservation for March Madness in April or May. (We don't gamble enough to count on comped rooms, though we usually end up getting one or two nights free.) After that inintial reservation, we check a couple times per week, cancelling and re-booking as the prices change. For example, as of today I've re-booked 7 or 8 times, reducing my overall cost by about $400 for the stay. We'll continue to check frequently until at least February.
But what I'd love to know is how the resorts adjust prices. They go up and down all year (sometimes rising significantly to coincide with a "sale"). I wonder to what extent a human being is weighing in on these decisions, or if it's all controlled by an algorithm tracking occupancy, market conditions, etc., etc.