You've a lot to "do". Your plane must be on time. You need a quick wait for your ME bus. You'll need to check into Pop w/ little wait. (If you're not on the dining plan, then you could grab a cab to CR & check in later.) I'm sure you won't be the only people getting off at POP from ME. Everybody will need to check in.
I don't make any ADR that I wouldn't mind missing for the 1st day. I've had planes arrive hours late.
Personally, I'd take the 9pm ARD and arrive early. (They will check you in up to 3 hours early.) Or, I'd schedule CM for another day.