The trips from MCO to the resorts on DME have been averaging about 70 minutes. There is no set route, there is no set schedule. Everything is dynamic to accomodate the most people in the most efficient manner. They have a schedule of approximately how many folks are coming in on what flights and plan accordingly. They try to group resorts by area, so most likely other stops on your route will be Contemporary and Grand Floridian, but never guaranteed.
You checked bags will not travel with you. Put the yellow tags on them, and they will be pulled behind the scenes and taken to your resort by truck. They are scanned several times, and delivered to your room as soon as possible after you check in. (Usually about 3 hours total) Yes, it is a good idea to pack in a carryon the items you need for your first day, and as insurance, what you need for the first 24 hours.
