We booked our 50th weekend at CR last year, only a couple of days after the 499 mark, and then tacked on a Poly stay a couple of months ago to extend the trip to 2 weeks. I honestly didn't want to go longer than just the 50th weekend but the Canadian border still being closed means that my partner can't come with me next month and our big trip has to be postponed, I figured we were already going that weekend so just put it for then.
Pre-Covid, October was starting to displace the traditional summer months as The Busy Time to the point where Disney had been offering free dining in the the summer, which was unheard of. The circumstances this year are ripe for a return to crowds imo. With pent up travel demand and more people being vaccinated (youth trials have already started), the 50th, school breaks, etc. I expect this October to be a madhouse basically all month, only possibly getting better after Indigenous Peoples Day weekend crowds leave. Especially if international guests are able to start returning. I'm not worried about crowds or getting things done because of the length of our trip, but yeah.