I'm not sure if you're using magical express or not. We did, and were surprised how fast everything went. We got on the ground just about 930. We deboarded, walked to ME, waited about 5 minutes, and were the second bus stop. We got off, went to the room for 20 minutes then got on a bus to DS. We were in DS before 1130. So it was less than 2 hours to touch down and get to DS. I wouldn't plan on it always working that way, but if you land at 1 I would say 3 at the earliest. I'd probably plan on getting there between 4/5 to be safe.
I, personally, would rather go the day we got there than the day we left. But if we had quite a bit more time on departure, I'd probably choose that.