DME has no trouble dropping you at one resort and picking you up at another. Just be sure they know this when you book.
What we have done when changing resorts mid-stay is this....we call Bell Services early in the morning and have our luggage taken away for shipment to the next resort. Be aware though...this is not a quick thing. It can take until late afternoon (5 or so) for your bags to get to the new resort. So, take what you may need for the day with you. Then, we eat breakfast and head to a park for a few hours. Then, we head to the new resort around lunchtime and check in. Sometimes we are able to get into a room. If we are staying DVC, then most likely we have to wait until later in the day to get our villa. But, we can swim or eat lunch or just head to a different park. But, we have checked in, gotten the phone number to call to see if our room is ready.
Then, later on the bags will be delivered to the room. It's really quite easy as long as you understand that your bags will be delayed.
Then, the day before you leave, you may want to doublecheck at the front desk that they have you listed for DME back to the airport.