When I book something similar it looks like this:
Arrive at RAC at my resort around 6:30 am & check any bags with the airline. I then walk over to the bell hop & check my carry-on bag. Then I head to bus/boat/monorail to MK & arrive in time for 8am RD.
At noon I leave MK & bus/boat/monorail back to resort (back by 1pm-ish). I pick up my carry-on bag from bell hop & am ready for my DME pickup by 1:45pm.
Now, lunch needs scheduled. So, depending on when dinner is...may eat early lunch in MK w/early dinner at MCO or would opt for later lunch at resort & later dinner at connection or final city. Either way there is plenty of time.
I've also been known to change clothes @ resort before DME or after arriving at MCO with a mini-sink shower out of courtesy to my fellow fliers that I will not get on a plane in my stinky theme park clothes from that morning. I literally pack a full clean change including socks & body wash cloths in my carry on.
Happy planning!
