Just to clarify.....you can only have your luggage taken, upon arrival at MCO, to the resort you are heading directly to, from the airport. Since you are heading to POR for that first night, your luggage would have to go to POR as well.
Now, compounding the issue is that DME doesn't get luggage after 10pm, and starts up again around 7am-ish the next morning. I doubt that if you left your bags at MCO, and they got them in the morning, they would get them to YC that day. It 'could' happen, but it's nothing I would try. Yes, you could book DME for the 15th, and then 'hope' that they grabbed your bags in the morning and got them to YC. BUT...the issue with tagging your checked bags, and allowing DME to take care of them, while you get to your resort in some other fashion, other than riding the DME bus, is that the DME luggage people have no idea how many bags they are looking for.
When you check in, at the DME area, they ask how many bags you checked. They then put that number into the system, so the luggage people know how many bags there are for each party. If one goes missing, they can start looking for it. You don't ride the bus, and give them that info, who knows what happens if a bag is misdirected by the airline...especially since it arrived the night before and just sat there!!!
So...yes, get your bags when you arrive, and drive to POR. Don't even bother unloading the bags from the car. Just drive them over to the YC that next day. You'll be much happier.