I still think you need to have an idea before discounts are announced if you can stay with a room only ( definitely not getting dining plan or tickets through Disney), or if you want to add the DP. Once discounts come out if you are changing/canceling that RO they can claim there are no rooms available for the re-book. At the very least you have a new deposit to pay and a wait for a refund.
Edited to add: of course I say this because I booked a bounce back/ split stay and then realized for the first time in my life the dining plans plus my TiW would save me money. That meant I changed to a package. Of course I then applied an AP discount two weeks later. Changing from the RO to a package was painful ( dealing with Disney).
maybe add in look at flights/pricing if air travel? Not sure what the timing is there but international flights come out about 11 months before, I think domestic 8 months?
cost of flights will affect overall budget for other things.
Any chance one of the smart folks on your staff could build a newer calculator to help people decide on this? It’s a question that comes up over and over and I feel like a lot of people just assume it’s the better deal and end up losing money over it. I know the one Joe and Ashley made get’s referenced a lot but it’s out of date. I think it would make an excellent tool in the TP bag of tips and tricks.
I know that there are different cancellation policies for “room-only” reservations & “vacation packages”.
These deadlines (while noting they could change at any time) should probably be noted in the time line?
(I know, this is so debbie-downer, but did you mention travel/trip insurance?)
Small thing but maybe add check online liner packing lists for liner must have items and suggestions for extra special items for families with kids - jewel, golf balls, trading pins, glow sticks, etc etc