When it comes to convenience, you can't beat the Wilderness Lodge or the Contemporary. Port Orleans Riverside is lovely, but it can't compare to the other two resorts since it is such a large resort (2.048 rooms at 314 sq. ft.) where guests must depend on buses to get to the parks.
The
Contemporary (655 rooms at 394 sq ft each) has a few extra perks. First, you can walk to the Magic Kingdom. You can come and go as you'd like without having to wait on transportation. Of course, if you'd prefer, you can also easily hop on the monorail to go to both the MK and Epcot. With the monorail going through the Contemporary Resort, it is often an attraction for young children, too. An extra perk is that you won't need to fold up your stroller on the monorail, either. This resort also has character dining on location at
Chef Mickey's. With younger children, it is nice if you have a Magic Kingdom view to be able to watch the fireworks from your balcony if you decide to wrap up the day at the parks early.
In comparison, the
Wilderness Lodge (727 rooms at 344 sq ft each) does have rooms that are a bit smaller, but I love the theming of this resort. You will need to take a boat to the MK (again, often an attraction for children), but this can be both a longer wait and ride. The boat is typically a large water taxi where you don't need to fold up your stroller. When visiting the other 3 parks, you will need to take a bus and fold up your stroller. Overall for me, the theming of the Wilderness Lodge is the best while the convenience of the Contemporary wins.
If we can answer further questions you have about the resorts or as you continue to make your plans, please let us know.