We've stayed at both WL and AS Sports. I don't know if this will help you at all since I know choosing a resort can be difficult but I'll try! To give you a little background, we stayed at WL on our first WDW trip and our children were then 22 months, 4, and 7. We LOVED the Wilderness Lodge. On trips after that we stayed at the BC, YC, and POR. On our trip last summer our budget was a bit slim so we decided to try Sports. I was hesitant since I thought we might be a little bit "let down" after staying at some of the other resorts. We did know what to expect though and we enjoyed it. BUT the difference for us was that on this trip our kids were 6 1/2, 8 1/2, and almost 12, so we spent a lot more time in the parks and less at the resort than when they were smaller. Since we spent such little time in the room this past trip, the amenities, and the room didn't matter as much. The pools are always full of kids and there's no slide. The kids still had fun but I know that my two that could do the slide at WL when we stayed there LOVED it. I also found the atmosphere at the pool at WL much more relaxing. Another plus IMO to the WL is if it was raining we could walk to the lobby to eat, shop, look for Hidden Mickey's, etc. without getting wet like you would if you are going from a building in All Stars to the main building/food court. Kids don't care about getting wet but I hate to get soaked and then walk into an air conditioned building. I preferred the food at Roarking Forks although it is much smaller than the food court at All Stars. We didn't have transportation problems at either place but we did enjoy the ferry from WL to the MK. At the WL you can rent water mice or pontoon boats, rent bikes, and enjoy kids' activities at Fort Wilderness. Sorry I'm getting so long winded. Bottom line is this...I don't think you'll be unhappy with either place and I doubt your son will be. If you are going to spend a lot of time at the resort and want non-park options, AND money isn't an issue I'd choose WL. If you are going to be spending a lot of time at the parks, not so much at the resort, and want to save the $$ difference to spend on souvenirs and food, then
pick Sports. We stayed in the Touchdown section which isn't extra $ like the Surf's Up buildings and is not hardly any further of a walk to the food court, and bus stop. Feel free to pm me if you have any other questions.