Hi Shelly! To stay or not to stay, that is the question!
Wilderness Lodge is such a fabulous resort, evoking the great rustic charm of the Northwest, as well as a nod to Native American culture. By the same token, Caribbean Beach Resort is a wonderful place to stay with plenty of hammocks to swing in and a newly renovated pool area, making it a welcome respite to a day at the parks.
The transporation from CBR primarily relies on bus service. At Wilderness Lodge, you have the option of using a boat launch to access Magic Kingdom, but must rely on bus service to access all other theme parks. Transportation for both resorts is reliable, remembering to allow a good 45 minutes for time from hotel to reservation. As Caribbean Beach happens to be one of Disney's largest resorts, the buses do get crowded in the mornings before park opening, and in the evenings when the parks close. The same can also be said for WL, however, at CBR, the tendency for crowded buses are more constant.
Hope this helps you plan your magical vacation!
-Malanie