Originally Posted by Host Young Gang Mom
fuscofamily5 had terrible experiences with transportation throughout the parks and hotels. We on the other hand never had a single issue (knock on wood). I think another issue would be how comfortable you are driving in new areas. Some can handle it better than others, it is too stressful for us to pick up and return rental cars and try to find our way around. The transportation issue is something you will find debated on most forum boards. I think it has it's pros and cons.
I want to clarify my "terrible experiences" a bit...
We've done Disney about 6-7 times with our children. Once off property so we drove everywhere, and once we drove and stayed on property and had a mix of Disney transport and self-driving, and several times we've flown and used Disney transport almost exclusively, so I'm not making a recommendation based upon a single experience here.
If you are patient and not trying to see as much as possible in a short period of time (as it seems your family is planning to do) then using Disney transportation is quite adequate. They run on time, they go everywhere you need to go and it's free/included.
That said, depending upon where you're staying and where you want to go you can expect to spend quite a lot of time sitting/waiting/riding on those buses and boats compared to driving yourself--and I'm talking about the equivalent of a day depending upon your needs. Indeed, going from one hotel to another can take over an hour each way at times when driving directly will take you 10-15 minutes. How much is that saved 60-90 minutes worth to you for a round trip? If you're eating in the parks and not visiting the other hotel/resorts the buses are pretty efficient and more direct and the saved hassle of parking and driving is probably worth it.
For us...we'll almost certainly provide our own transportation in the future, at least for going out to eat as we enjoy trying the better restaurants at the other resorts and having the option of going off-property to buy groceries and eat.