Im sure Ill change my mind 300 times before we leave next december, but right now I think id like to fly in the morning before and stay at AOA, and then catch the magical express from the resort to the port the next morning. Correct me if im wrong, but do you need a park ticket to stay at a WDW resort? Or do they not care if you booked a cruise?
No, you don't need a park ticket to stay at the resort, or to use DCLs ME.
but, I do think you need at least a one day ticket to get the Magical Express from MCO to your resort (don't quote me on that, but I think you need at least a one day ticket to get the Magic Your Way, which includes the ME from MCO to the resort)
If you fly in the morning...lets assume you land at MCO around 10a....you will be at AOA and checked in by noon or so, and could be at one of the parks by 12:30 / 1p...and that's a relaxed schedule. It worked very well for us, and I had an 8 year old in tow! They had our room ready when we arrived, but if that is not the case for you, you can check your bags with bell services. Or, if you use the luggage delivery feature of ME, you can just check your walk on luggage with bell services and head off to the parks. When your room becomes available, bell services will deliver your luggage to the room. No need to sit around and wait.
The night before you leave for your cruise (so, same night for you) you will get a packet from DCL delivered to your hotel room that has green DCL luggage tags for DCLs ME, as well as instructions and departure time / location for the following morning.
The DCL ME is separate, and is booked through DCL. As I recall, it is $60 a person, round trip. They can pick you up from a WDW resort, and drop you off after the cruise at WDW or MCO. Alternatively, as I mentioned, the same service is available departing from MCO as well, so you could stay in a local hotel, and then taxi or hotel shuttle back to MCO in the morning.