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Friendly advice: DON'T DO IT!
I don't think the bags wil be delivered. LOGISTICALLY, there is very good reason for this.
When you do a split-stay, you have two totally separate WDW reservations. You have two different reservation numbers, one for each stay.
Each DME tag has a barcode. The barcode is basically a computer-ese version of your reservation number. If they scan a barcode for a reservation that is in the future, they won't know how to route the luggage. In other words, IT WON'T COMPUTE. They might leave it hanging around the airport luggage-sorting facility for a few days until the reservation starts.
Basically, you can't use DME before your arrival day. You would be trying to use the DME luggage service prior to your arrival day for the second reservation ... you WILL have luggage problems if you try it using the second set of luggage tags.
A second set of tags (for the second resort) is sent out as part of a long-standing computer glitch. For every reservation number with a DME reservation, DME generates a complete DME packet, which includes tags. However, there is NO NEED for DME tags for a second reservation as part of a split stay.
My strong advice is don't even try.
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