Whatever you decide, know that things take a lot longer than you plan on. For that reason, I'd keep it simple and, preferably, close to where you need to be.
I always think along the lines of, my flight lands at 9, I can get the car and be at the resort by 11. But then there's the lunch stop. And the Target run. And then the room's not ready. And then it's a lousy room, and I want to see if I can change. And.., well, you get the idea. Same goes for planning things after check-out and before the flight back.