If you take money out of the equation it's a no brainer. WL is far superior in pretty much every aspect I can think of (including unfortunately the price
). If you can afford it WL would be my vote. If budget is a concern then Pop is pretty nice and superior to the all stars IMHO. I know you said Port Orleans is out for you, but Coronado Springs is a really nice moderate if you are looking for middle ground.
I have seen up to 30% discounts offered this year for deluxe resorts so you probably have to do the math and see if the free DDP is worth more than the discount offered when you are booking. It takes a little time to do, but if you map out where you want to eat and crunch the numbers you can see if for you DDP is really worth what they charge for. If you plan on doing a lot of character meals or tend to order more expensive items at sit down restaurants it can come out as a gain. If you sometimes just might want a salad and/or an appetizer then it can be less of a value.
Another option to consider is renting DVC points at Wilderness Lodge from an owner or through a rental site. You can usually save a bunch of money over rack rates, but you wouldn't be eligible for free DDP. A week at WLV is 107 points in a studio. If you rent from one of the reputable sites at $14 per point you would be paying $1,498 for the room for the week ($214 per night). Rack rate at WL is $361 per night for the same time. Renting a DVC villa would save you about 40% off rack rates. Rack rates for rooms at Pop Century are around $130 a night for the same time.
When you start to look at DDP it gets a little more complicated. To buy DDP for a week for 2 adults and a child is $973 or $139 per day. If you rented DVC points for $214 a night and bought DDP for $139 a day you would be pretty much right at the same cost as paying rack with free dining. If you think you would spend less than $973 for meals then it may be worth just paying out of pocket for meals and renting DVC points.
Just to compare, a room at Coronado Springs rack rate is $210 a night. If you got free dining it would cost you $1,470 for a week. Compared to $2,527 at Wilderness Lodge with free dining. Pop would run $910 plus the up charge to go from quick service to regular dining plan (last year's price for 2 adults and 1 child would have been $37 a night or $259 total). With the upgrade it's $1,169 for Pop.
For me it's well worth the extra $300 to go from a value to a moderate. Size alone is a huge advantage. There are almost 3,000 rooms at Pop vs a little under 2,000 at Coronado Springs vs about 900 at Wilderness Lodge. The bus service is impacted by the number of rooms. The moderates have better dining options, slightly larger rooms and nicer resort amenities. The main pool at Coronado Springs has a pretty cool water slide.
The bump up to a deluxe is a little more steep. The huge advantage of Wilderness Lodge is that you can take a boat to either MK directly or to CR where you can catch the monorail to either MK or EPCOT. With a 3 year old you are likely spending a lot of time at MK. It's great to not have to take the bus there. You also have good dining options nearby. Whispering Canyon right at WL and Chef Mickeys at CR are great (especially for kids). You also have Mickeys Backyard BBQ nearby at Fort Wilderness and Ohana at the Poly is very popular. The rooms at Wilderness Lodge are also nicer and bigger. With a 3 year old taking naps or at least having rest time you will probably spend a little more time in the room than some people do. The extra space could be nice and you would have a balcony to escape to if the little one is asleep. On our last trip we stayed at Bay Lake Tower and enjoyed a few adult beverages each night on the balcony after the kids went to bed. It was a nice way to unwind. It probably comes down whether you think the advantages are worth the extra cost.
