You'll have fun whatever you do. I'm personally a fan of timeshare resorts as long as you don't do a timeshare presentation. It just feels calmer offsite and they are such nice quality places for a great price. When I had little ones they enjoyed the hotel swimming as much as the parks, so a nice peaceful resort like the Windom Grand was a real plus.
But really and truly, do whichever appeals to you more for this trip. Do you want to be in the bubble? I usually prefer outside, as inside I feel trapped to eat Disney food and stop in more Disney gift shops that I care too as they are all over.
Another consideration: Is your child one who will be enthralled with the larger than life icons/statues/decorations of a Disney value? If so, maybe do that. When DS was five or so he was really into Herbie the Love Bug, so my parents instead of their normal offsite lovely condo on a short stayed at All Star Movies (called it the Herbie Hotel) for a few nights with him, as he wanted to go there. Has your four year old made any special requests (probably too young)? In our case, DS had found out about this place on behind the scenes info on one of his Herbie movies and said he'd love to go there sometime if he could. My parents requested that building, had him wear his Herbie shirt and carry his Herbie car, so they'd have a really good chance of them giving them the building they requested too (How can you put a kid wearing his Herbie shirt and carrying his Herbie car who wants to stay in the Herbie building anywhere else?). He was do delighted with the statues, wall paper, photos, everything, and that this made staying in a less luxurious place for a short while so totally worth it.
With the exception of something like this, I'd do the Wyndham unless you want to be in the bubble or care a lot about onsite perks -- transportation, earlier fastpass selection. I usually value a nicer/calmer place more than these things.
