The new system can allow for 60 days out.
But the new system isn't really working so well. I have, apparently, checked in for our 4 room-only stays coming up, and did so a few weeks ago. It took a LOT of time, and wasn't without error messages and systems going down and just flat out not working, but it seems to have worked. Set up a CC for charging (we don't actually charge to the room, but it will NOT let you not do it) with PINs for each person (that's new), had the opportunity to make up to two choices that are given for your specific resort, put in what time we'll be arriving, etc. And when I log back in to my account it shows that I've already checked in. So....