In general, you can expect that the DME bus will deliver you to your resort anywhere from 60-90 minutes after you get off of the plane. The average reported is about 70 minutes. That's assuming you use the DME luggage transfer service or have only carry-on bags. If you are collecting your own bags add at least another 20 minutes to that time.
DME will deliver your luggage to your room within about three hours after you check in to your resort; assuming that your room is ready at that time. (If, for example, you check in at 9:00 a.m., it's possible that your room won't be ready until 3:00 p.m. and obviously your bags would not be delivered before that.)
One important thing to note is that there is no reason to wait for your bags to arrive in your room. (You should have anything you need for the first 12 hours of your trip in carry-on bags in any circumstance.) The bags will be delivered even if you are not there and not having to hang around is one of the best parts of the service.