For an 8pm arrival time, I would figure on resort arrival time to be about 9:15-9:30. Bags may not arrive until close to midnight though. The value resorts tend to have slower baggage delivery service, so I would really recommend having the bags held until the next morning..if you allow DME to deliver them for you. You could also leave the tags off the checked bags and collect them yourself upon arrival at MCO. Yes, that will add about 15-20 mins to your overall time, but you will have your bags with you when you arrive at the resort.
If you decide to let DME take care of them for you, tell the front desk, at the resort, to hold your bags until the next morning. Then, stop by the Luggage Assistence area and tell them the same thing. Then, when you get to your room, put out the 'privacy please' hanger on the door...that way no one will disturb you if the luggage hold instructions fall by the wayside. The bags can be delivered first thing in the morning.
In any case, always pack a carryon bag with anything you may need that night...just in case the airline misdirects your checked bag(s). If it were me, I would leave the checked bags untagged, then go to baggage claim, get the bags myself, take the bags with me to the DME area, have then stowed beneath the bus and have them when I got to my resort, vs waiting for them to be delivered via DME.