WOW! You guys have me thinking now! I appreciate all the great feedback!
I'm starting to think that a value might be the way to go. Start with something like POP or AOA and work our way up. I think its important for DS5 to see things that are "cool" and seeing BIG signs and characters would really blow his mind! The tough thing I've spoiled the wife with multiple stays at the Portofino Bay. She's used to Club Level and and all the perks that come with staying in a Deluxe. I don't mean to make her sound like a snob or something. She just like to vacation a certain. Should I consider a split stay if this doesn't fly? 5 days in the Value. 5 in a Deluxe?
The value properties look adorable, but, having stayed in one once, I'm going to suggest that, since you can afford it, stick with a deluxe. Because, despite their cute themes and bright colors, etc., the values all have paper-thin walls. If you get especially unlucky and have slightly noisy neighbors, you could be in for an uncomfortable, to say the least, stay. This happened to me once, and the resort couldn't move us because it was booked solid. At the time, I didn't think to just move to another resort altogether, but, had I thought of it, I would have. Sleepless nights at WDW are not a good thing. BTW, I'm not the only person who ever stayed in a value to mention this problem. And since your wife is used to staying in deluxe accommodations, I would seriously advise against a value resort. The mods have much better noise insulation, and the deluxes even better. Yes, you can get obnoxious neighbors anywhere, but I've never once had a noise problem in a deluxe.
Also, your son is 5. I'm thinking you're going to be spending a lot of time at the Magic Kingdom. For that, you can't beat the monorail resorts, especially the Contemporary, since you can walk to MK from there. Even WL is a good choice, since there's a fun boat ride from WL to MK. And, also, if your DS is into animals at all, consider Animal Kingdom Lodge. Yes, it's not as close to any of the parks, except Animal Kingdom, as other resorts are, but there is so much to do there and watching the animals is a treat in itself.
I know that lots of people love the values, and that's great. But, without being snobby about it--just thinking what your wife enjoys and has come to expect
and that you can afford--you might want to focus on the deluxe resorts. You don't have to stay club level to get the most out of them, and keep in mind that there are discounts for nearly every resort most of the time. You just have to keep an eye out for them and pounce when they're released.