Hello Andrea,
You ask a great question!!! And with your question, I want to ask you a question. How much time do you plan on spending at the Disney resort? For my family, the only time we spend at our Disney resort is sleeping and eating breakfast. The rest of the day, we are having the time of our lives at one of the Disney parks!!! So, my family will always choose the more economical resort.
Now, if you will spend a lot of time at a resort enjoying the beautiful surroundings, awesome accommodations, and an INCREDIBLE pool, then your family will want to spend an extra thousand dollars and stay at the Wilderness Lodge. The Wilderness Lodge is breath-taking!!! Port Orleans Riverside is a nice resort, but the Wilderness Lodge is in a league of its own.
As you are making your decision, it is also nice to know that the Wilderness Lodge rooms (340 sq. feet) are bigger than Port Orleans Riverside rooms (314 sq.feet) While you think an extra 26 sq. feet will not make a difference, you will be amazed what a little extra room will mean when you are trying to get your one year old to sleep or to take a nap.
I hope this helps you in your planning! If you have other questions, please let me know!
Have a MAGICAL day!!!