I think the 5000 days are gone. You should spend some time looking at the Redweek ads to see what weeks have lots of listings, and which have lots of already rented and what the asking price was. There seem like a ton of 4th of July and end of March weeks available, maybe those will rent closer to the date, or maybe it can be hard to unload weeks even though those are popular travel times.
I've been looking for an OF rental and been having a hard time finding one. Our break was always at the end of March and I always found something, and a good deal at that. We since moved and now our break is near the beginning of March and there are much fewer options.