My kids were all about all the play spaces/playgrounds. They are still convinced (3 years later) that any ride on Dumbo at WDW without getting time the play space first is a waste of that attraction. And Epcot had several playgrounds setup during the F&G that they requested to visit multiple times in our 2 days, in addition to the aforementioned hour at the Mission Space play space. And then the Boneyard, oh the Boneyard. If I didn’t have the promise of collecting every single Wilderness Explorer Badges possible to lure them out of there, I don’t know if we would’ve made it out in under 3 hours! 
Our planned trip overlaps most days with Prophet Paul AND we are almost the same demographic group, minus a 1 year old - my grown DS and DDIL, their 26 month and 4 year old sons and my DH and I (the grandparents!). I have enjoyed reading all the plan updates and have a lot of the same elements in my own plans, but I have to echo davej here - I worry Paul, that your plans are a bit aggressive.
I’ve done DW about 14 times but this will be the first time with our grandchildren. I’m doing all the planning for our group and have left most days open past ~2 or 3pm (except for 5:30ish dinner ADRs) and have only planned 2 evening events out of 7 nights that include the kids. (One night is before a late start day and the other is our last night.) We plan to have the adults take turns going back to a park some nights (two stay with GSs, two go have fun). We are focusing on keeping the kids well rested so we can RD each morning and have (hopefully) relatively happy kids. They normally don’t stay up past 7:30pm so we worried we’d really be pushing it with going back to parks at night. Maybe they will nap in the strollers but we didn’t want to count on that or it being enough. And don’t forget, many of those afternoon breaks end up being only an hour or so once you factor in the transportation.
Now - of course you are a runner so I assume you have a ton of energy and must be skilled at parenting 3 young children (and one with health challenges) so obviously you know your own kids. I just worry your trip may become too stressful for you - don’t forget it can be hard to cancel events at the last minute (hopefully Bump & Dump continues to work). Maybe consider dropping the early morning Chef Mickey’s, for example and sleep in? (You have plenty of other character meals.) And your first day - everyone will be up really early to make your flight I assume, so do you really want to start your vacation with the kids up late that night for HEA? We plan to just pool it and then get the kids settled in that first night.
Anyway, please accept this unsolicited advice from a total stranger - for what it’s worth
It’s obvious this trip means a great deal to you so I really hope it is truly magical for you and your family. We should look for each other on the 27th when we will also be at MK - with an 11:35 Parade package at Tony’s!
Thanks everyone for your thoughts and advice. I value your input greatly. I will probably end up gambling on an evening activity 2 or 3 nights, and will plan the remaining to be super flexible in case we don’t return to the parks after naps. I’m confident DS4 will be able to do the later bedtimes, just not sure about DS3. We will probably just split up in the evenings, and having the grandparents with us will give us even more flexibility.
Please keep us updated on your plans though! I love reading them and it’s helpful to see what you will be doing over our same dates!
I agree with one of the posters that slimming it down a bit is wise. It is a very, very, very ambitious plan with three kiddos under 4 and grandparents in tow. I know it’s just a plan/sketch at this stage with lots of time for tweaks, but you have RD/early AM plans every single day of an 8 day trip AND also late evening plans (FEA, Illuminations, Halloween party, s’mores etc on most days too) Plus: table service ADRs with 3 kiddos, 2x/day and even 3x/day.
On your first night you will get back to your hotel at 10pm (or later depending on when FWs are) and then have to turn around the next AM and rope drop, then rinse/repeat. I went to WDW with a DS6, DS 9 months and 3 grandparents plus spouse and they would have staged a coup had this been the schedule
but they admittedly have lower park stamina than some. But, i also went to DLR with a DS2 and DS7 with my active Mom and ditto. I’m now planning an 8 night trip for my DS5 and DS11 with spouse, and am planning 4 RD days (which is probably two more than my family would prefer) and 4 very late start days (ie, 3pm). I can foresee you having to nudge your family along from one ADR to another, worried about cancel fees if you miss, although the bump and run is s good back up in case.
Two things stand out to me that might be helpful to think about:
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I You are looking at 3-4 hours a day sitting at restaurants. I find TS service at WDW and DLR to be very slow, especially dinners. Someone needs to walk around the baby, someone needs to play games with older kids… you might want to pare back.
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very likely many in your crew will not have your stamina to return to parks in evening after an exhausting late night/RD schedule (I’d join you though! My husband tells me that only my Mom and I get more energy from parks as the day wanes, and everyone else just gets plain tired!) . We did two straight days at MK (first day RD to 6pm, no return to park, and the second day RD to 2pm, with return to hotel for naps and then 6pm Thanksgiving reservations. We all overslept we were so tired. Great dinner but then only 3 of us (DS6, me and spouse) returned to parks for HEA, even though the next day was completely sleep in with no plans till afternoon. Everyone was TIRED with a capital T but grandma graciously offered to put down our little one for a good night’s sleep so my husband and I could take our DS6 back to MK. Memorable evening and SO happy we went back!
Some things to consider:
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you should have a HUGE advantage on FPs with rider swap and such a large group (5 paid tickets). When we were there with our 9 month old, we split up our FPS into pairs for headliners with Rider Swap, Ie. 3 SOarin FPS, with rider swap turns into 6 FP. Not sure if it still works that way but if it does, you shouldn’t need to RD Soarin. DEF go in with a RS FP advance planning.
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I might suggest doing Halloween party when kiddos get older or just have grandparents babysit for a parents night out.
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I’d consider dropping GG and either Chef or Park for breakfast. Give yourself s break in the AM from having to rush out door.
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Epcot is a great park to do a half day TP (ie: TP has an afternoon plan in future land as well as a WS one), and thus it’s a great park to put following an HEA evening or F! Evening, especially so since you already plan to go twice. Both days in my plan where we stay out late the night before we have a late start in Epcot, easy to do when you do two days and easier for you b/c you have the golden ticket Rider Swap set up! You could let kids have pool time AM, get them down for an early nap, then head over and stay thru illuminations. You’d still have to choose FEA Tier 1 for a different day but you could do 2 FPS for Soarin, and 2 for Test Track …read up on tips for this.
In the end, have fun and please post back here. I personally LOVE your take the WDW hill mentality, but you may have to postpone a few things for when your kids are much older or on an trip sans kiddos!