First, it's supposed to be delivered within 3 hours after you arrive at the RESORT, not when you land at MCO. So, assume the "normal" 90 minutes from deplaning to arrive at the resort, and you're looking at four an a half hours after you land before expecting your luggage. That's 11:30P.
Second, you should ALWAYS, ALWAYS, ALWAYS, have enough clothing/medications/whatever with you as carry on to support you for the first 24 hours. This has nothing to do with DME, and everything to do with airlines possibly misdirecting your luggage.
Third, collecting your luggage before going to the DME pickup location will take at least 30 minutes, potentially slightly longer if your airline delivers luggage on the A side of the airport (DME is on the B side).
Personally, if it was me, I'd let DME take care of my luggage and make sure I have what I need for the first 24 hours. When I was ready to go to sleep (if the luggage hasn't been delivered), I'd call luggage services at the resort and ask them to hold the luggage until the next day.