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, [B][U]you can’t use DME before your arrival day[/U][/B]. 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.