DME info packets tell you to expect your checked luggage, in your resort room, up to four hours after resort checkin. Only one time has it taken longer than that for me.....and I've used DME many times to date.
Do a lot of people not tag their bags and then go to baggage claim to get it and bring it to the DME bus with them? In a word, no. Luggage delivery is one of the best things about DME.
Pack anything you are going to need for the first day of your stay in your carryon bags. I usually have some small toiletries (3oz size for TSA regs), a book, my swim suit, teeshirt and shorts, underwear and some snacks. That way, I can do one of several things when I get to my resort...
1. I can change and go for a swim and grab a bite to eat
2. Change, if needed, into shorts and hit a park.
It really is a good idea to pack your carryon like this in any event. Airlines do misdirect bags, so it's good to have what you will need with you.
When a lot of people do not tag their bags, and get them at baggage claim, it bogs down the whole system. If the driver has to stow a lot of luggage, it delays departure from the airport, not by much, but a bit.
The big holdup comes at the resort level. That driver is going to stand there, waiting for his tip, from each person who has stowed baggage. That means that rather than a 3-5 min stop at each resort, it can be close to 10 mins...that really adds up, especially if you're the last stop of three resorts.
This is one reason I hesitate to continue using DME. It 'should' take about 55-70 mins to get from the plane to your resort. But, with more and more people choosing to get their own luggage, it changes that timing..making it closer to 90 mins.