We took our kids several years ago. I think they were around 7 and 9. Once was enough. While the scale of the operation is amazing, it's just so manufactured. IF I was going back I would most certainly stay off the property and just buy a day pass. Watching grown adults, who haven't ran in 20 years, run and fight to get in line at rides when the gate opens is a sight to behold. Or the grown man with his family, standing inside the Holleywood Studios gate, crying like a baby, telling his kids "We made it!" It's all very gimmicky to me.
We stayed at the Art of Animation Resort. Fair warning, all the of the Disney Resorts are not created equal. The "cheap" ones are just that, cheap. The fancy ones are MUCH nicer but obviously way more money. We stayed at the "cheap" one thinking they were all sufficient and we wouldn't be there much anyway. Big mistake. We got some Under the Sea room that was basic and at the far end of the resort. We walk 20 minutes, and open the door to a room that was less nice than your average $100 a night 2-3 star chain hotel. My daughter takes off her shoes and jumps up on the bed. I look at the bed and it's covered in brown and wet footprints. They'd just cleaned the carpets(poorly) and the floor was soaking wet. WTF. So I call the front desk and ask for a different room, but that's going to take hours. The family decides to go to the pool while I try to make the switch, my bag was stuck with the complementary bag service so I've got no swimsuit anyway. I finally get to the second room. I walk in and there's a nice crusty pepperoni on the floor and hair all over the bathroom door and shower. Now I'm pissed. Many hundreds of dollars a night for a Motel 6 room.
We stayed in that room for the night. The next day we're at Magic Kingdom waiting in line(naturally) and I can't let it go. I can sleep in a tent on a mountain and not shower for 10 days, I'm fine with the basics, but not when I'm paying that kind of money and got sold a bill of goods. I call the resort and demand to be moved to a different resort. Finally they offered us the Lion King Suite at our resort. Fine, it's something. It was much larger and clean, but still more run down than I would have expected.
My kids had fun but it wasn't some life changing trip. We've taken to them to Costa Rica, Alaska, and all over the US to beaches, mountains, and lakes. Hunting trips, road trips, etc. I can't remember the last time they mentioned a fond memory of Disney. I hear about San Diego, fishing in Alaska, or the animals in Costa Rica all the time. Those ones stuck, Disney did not.
Going to Disney is like some parental right of passage in this country and it's odd. "Oh you have to go just once." No you don't. But if you do, just enjoy it. Outside of our room mess I had a good enough time, but it's not magical magical experience to me, nor to my kids. We're going to drive the coastal highway this spring from top to bottom and the kids are far more excited about that. And that's about 1/4 the price of Disney.