With a 9am flight, you will be picked up around 6ish...give or take 15 mins either way. If you choose to use RAC to check your bags you will be able to do so, but be at the RAC counter no later than 5:15am. You must be walking away from the counter no less than 3 hrs prior to your flight departure. It can take up to 15 mins.
For your arrival.....it can take an average of 75 mins, from gate to resort. I've had times as short as 55 mins, but one time it took me 90 mins. I've used DME so many times I can't remember how many times I have taken it.
As far as bags go...the DME info packet tells us to plan on getting our luggage delivered to our rooms within 3-4 hrs of resort checkin. Note, that is resort checkin, not when you arrive at MCO. And depending on what time you get to your resort, your room may, or may not, be ready yet. And if the room isn't ready, there is no way you will have your checked bags. No room for them to be delivered to.
Also....the resort you are staying at will make a difference as well. The value resorts don't have luggage delivery nearly as often, or as quickly as other resorts..so it can take a bit of time. But you can plan on getting your bags, in your room, about 3 hrs after resort checkin.
Be sure to pack anything you may need to start your fun in a carryon bag.