I would suggest that you make a cash ressie through CRO and be prepared to stick with that if the rental plans don't work out.
The problem you will face is the period you have selected is very, very busy. In all probability, the only way to get all those dates is to have the owner call every day (day-by-day), as soon as MS opens, and hope for the best. And, of course, every other owner who wants to go during that time will be doing exactly the same thing.
DVC owners can make ressies at their home resort exactly 11 months from the date of check
out, as Deb indicated. You said in your original post your checkout would be Jan 2, so you would not be able to have your owner call for
that date until Feb 2.
The owner you are renting from could call for your
arrival on Jan 21, and again on Jan 22, Jan 23, Jan 24, etc. But if they were unsuccessful anywhere in there, they would have to either abandon the rental or go on a waitlist. To make matters worse, there are two weekends during that time they'd be calling, so they'd have to be successful for
both days on each of those Monday morning calls...and they'd have to be successful
twice! That's hardly a strategy made in heaven.
The likely result is they would have to waitlist, and they'd get some days and not get others. That's a tremendous amount of work for an owner to do, and the prospects of success in putting together a trip that long, during that period, are not very good.