I was hoping you'd give a report of how things went

I saw on the family board that you guys were there for Thanksgiving. Hope your MIL had a good time.
I am really looking forward to our June stay. I'm glad we'll have a car, just in case we run into a similar AK situation. I completely forgot about the boat to WL. Maybe we'll do dinner at geyser point or something on our arrival afternoon. I hate to make ADRs on arrival day. Never know how fried the kids (and we) will be after arriving via car. So glad to hear about the community hall and open spaces. My kids neeeeeeed that. Ha. Last summer used a community hall for the first time - it was a great place to go during a sudden thunderstorm when we were enjoying the OKW pool. My kids could have spent all afternoon in the community hall.
So glad you had a great trip!! When's the next one??
We're going over Easter break! (another busy time ... now that our older kid is in school ... but we will be going for a longer trip and will plan to take some resort or water park days. Also, the crowd calendars aren't *as* bad that week)
We almost always make an ADR on arrival day, but make it a low key one at or near our resort. Since we fly, we usually have a better idea not only of our arrival time, but how fried we all will be. Our kids LOVED Whispering Canyon; our 3yo keeps shouting "We need ketchup!" The Wave at the Contemporary usually doesn't need an ADR and is pretty relaxed, so maybe keep that as a backup if you need a comfortable sit down place to eat. We usually go to dinner between 5-6 as that's the only chance we have of getting the kids to bed at a reasonable hour.
For your kids, I'd also suggest Mickey's Backyard BBQ at Fort Wilderness - but bring ear protection because it can get loud. The food (barbecue buffet) isn't the best, but there's a lot of dancing and character meets for the kids, and a nice boat ride to and from. We took our kids when they were 4.5 and an infant. Our ODD LOVED it. I've also heard good reviews for Hoop de Doo, which we will try when the kids are older, and we are trying Artist Point with the Snow White dinner next trip.
We've also done ADRs at all the monorail resorts when we've been staying in the MK area. 1900 Park Fare is a favorite, as are Kona Grill at Poly and Ohana.
Edited: Also - taking the monorail and the security check was not bad, even with a double stroller. Despite the parks being very crowded, Disney CMs were amazing at helping people get on/off, helping my MIL with a
scooter her first day (then she refused to take the scooter on the monorail again, but that was her choice), and generally keeping things moving. The only longish lines for security checks were at the entrance to Epcot (we had to go through security before going up to the monorail platform at the Contemporary, and again after getting off at Epcot and before entering at Future World. In the future, if we weren't trying to rope drop anything in Future World, I'd take a car to the Boardwalk area and enter at World Showcase.