DME needs 10 days to get packets printed out and sent to the guest, so no, I doubt he will get anything.
So...he gets off the tram from the gate (everyone takes it). He has two options here...he can get his own luggage and bring it to the bus with him, or he can go directly to DME and have someone else get his luggage from baggage claim and take it to the resort. So....If his plane lands on Side A of the terminal, he can go down to baggage claim on level 2 (he arrived on level 3), get his bags, then return to level 3 and cross through the main terminal to Side B. If his plane arrives on Side B, he just goes there directly (no need to do anything special). He now goes down to level 2 and gets is baggage there.
If he chooses to not get his own bags, he goes directly to Side B, level 1, described below.
Okay...now he has his bag, and is on level 2, Side B. He now goes down one level to level 1, ground transportation. All the way at the end of that area you can find DME..it is after the car rental counters and Mears counter. If bags haven't been picked up by your friend at this point, he will go up to the counter, give the CM his baggage claim receipt and a description of the bags. Someone will be sent to get the bags from baggage claim and get them to the resort.
If he has the bags in hand, he will go to the bus and the bags will go beneath the bus in storage and handed off to him when he gets to his resort.
Either way works....just depends on what he prefers to do. If it were me, I would get he bags myself and have them in hand.