My dd and dh arrived at MCO at 10:15 pm last month. They had only carryon so checked luggage wasn't an issue. They were at POP by 11:00.
If you are checking luggage, I would't put the yellow tags on them. Then I would just grab the bags myself and bring them to the DME desk and have them put on the bus. Otherwise, if you put the yellow tags on them, they will be pulled before they even get to the baggage claim area, put on the truck and who knows when they would get to the resort....most likely within a few hours but do you want to have them being delivered to you that late? I wouldn't so hence would grab them myself, the old fashioned way. But, arriving on a late evening flight is the only reason I would have for not using the yellow tags and having DME pick up the bags and deliver them to my resort.