Don't remember where I read this but they said on the way BACK to the airport that the luggage will travel directly with you on the bus so I would say no to that leg of the trip.
I would bet that Disney would just do a sweep of those with the luggage tags at the Orlando airport so they would get your bags to the resort for you. Thinking there may be some sort of color combination according to the resort area to put the luggage on different trucks.
There are times where the bags beat you to the airport, when you miss a tight connection, but the bags make it. If that were the case, I would not think that they would leave the bags until they made sure you were on a bus on your way to the resort, which could be hours away. Instead, I would think your bags would be waiting for you. Of course this may be different, but that is how I would think that it would work. We really won't know until someone tries it once the system is up and running. You could try emailing or calling Disney directly to see what their stance on the situation is.