Hi OP. I have a double BOB stroller and have stayed at the WL with it and BLT (and the CR before kids). If you can swing the extra $$$, I would pick the CR. Our WL trip was almost your exact dates in May. We really loved the resort but the CR transportation options are so much easier with kids and with the Bob, you will need it. The boat to the MK during our stay alternated the small boat with the larger boat. You cannot roll the stroller on the small boat and because of its bulky fold, it's a little difficult to get on the smaller boat. There is one larger boat tht they had in use a couple of times that has a different entry in and you cannot get the stroller on if anybody at has entered with a ecv, a wheelchair, or another double. Also, WL has only has bus options for the other 3 parks and once again, BOB is difficult. I cannot say enough about the ease of the walk to the MK and the monorail to Epcot. Have fun planning.