How far in advance do you checkin?

We have done it month's ahead as well as just a few weeks ahead, just when I feel like it. I do make sure I give my room requests over the phone and have it added to our reservation. I always skip that part when doing the online check-in.
 
I just checked in for my stay in early Jan after giving my room request to DVC member services.
 
I do it a day and sometimes day of, usually around when I'm checking in for my flight. I've still received my room requests without issue. Part of it is just conflating checking in at Disney with what "check in" means almost anywhere else, even though those things are different. I don't want to accidentally commit myself in a way that I can't undo. And even though that's not how Disney check-in seems to work, I still just wait until I'm absolutely sure that nothing is going to change about my reservation.
 



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