Hi there, Megan!
Disney transportation is definitely vast and varied, and planning routes can become quite a task.
But with a little bit of forethought, you'll be navigating like a pro.
Start at
Disney's official Transportation page, where you'll discover a nice breakdown of what mode of transport will take you to what destination. From there, you can start planning out your routes, based on your destination/s each day. If you need some further guidance, drop me a note with some of your itinerary, and I'll be glad to provide you with some samples of "best routes."
You can also search online for "best way to get from ______ to _______." Unaffiliated fan sites provide a wealth of knowledge from seasoned travelers who have perfected the art of the Disney route!
And yes, sometimes the urge to drive is pretty strong. And if you have young children, you might want to consider the car.
The choice becomes one of freedom versus no hassle: When you drive to Magic Kingdom, for example, you'll park at the Transportation and Ticket Center, and hop a monorail or a ferry over to the Park. If you use Disney's bus from the Caribbean Beach Resort to the Park, you'll be dropped off virtually at the gates. But a car won't require a wait - ever - and you won't need to build in as much time for transportation during your trip (a Disney bus, for example, makes multiple stops at a Resort, while your car will take you straight away!).
Feel free to let me know your biggest "how do I ... " queries, and I'll be glad to help get you moving in the right direction.
See you later, celebrator,
-Deborah B.