Hi,
I hope all your wildernesses lodge experts can help me out.
My family has not been to Disneyworld since 2008, and we are now looking to take our kiddo for a week in October 2020...
Should I book a room only or package option now?
Also I’m booking based on a school year calendar for this fall and there is a chance it might be off by a week next year is that easy to change.
Personally, regardless of whether you book room only or package, I would make two reservations, one to cover each possibility for the vacation week, and then cancel the one you don't need as soon as you know. That way you ensure you will have the room you want at the resort you want. But we are also a family that books a room only reservation at 499 days out and is willing to pay rack rate to ensure we have the hotel/room/dates we want. Of course, booking two reservations also locks up those funds.
I would also reach out to the school board and ask if they have their 2020-2021 calendar already -- they may even if they haven't published it yet.
As for room only vs package, things have gotten more complicated because of how WDW has changed the structure of their ticket pricing. Ticket pricing is now tied to the specific dates you are visiting [they do have a "any date" option] and is good for a certain number of days within a certain number of days of a "start" date. Then, to complicate it, stand-alone tickets will have a defined end date, while tickets bought as part of your on site stay are good for that stay. That difference may not matter if most of your days are park days, but has implications if you plan on lots of non-park days. To illustrate using random date of stay:
A 3 day, 1 park per day ticket purchased as part of a WDW hotel package stay of Dec 13-19 2019 is valid for any 3 days from Dec 13 - 19.
A 3 day, 1 park per day ticket purchased as a stand-alone ticket from WDW with a start date of Dec 13 expires on Dec 17.
You also have to decide on whether you want a dining plan or not. I have sat with a spreadsheet and for our family, it isn't worth it, so we don't do it. YMMV and there are many reasons families get the dining plan, not all of which are cost-related.
Room only and package have different rules related to them. Room only requires a deposit of one night up front and can be canceled upto 5 days before the trip. Packages have a smaller deposit but their cancelation date is further out from the trip. There are other differences that it is important you understand before making the decision of which is best for your family.
Once you make the decision of whether you want room only or package, then it comes down to when to book.
For our family, we always book as soon as we can/know we are doing the trip and booking is available. For us, since we are usually booking room only, that means booking at 499 days out to ensure we get the dates, hotel, and room type we want. Although it is rack rate, we book where we want to stay and would be ok paying rack rate if there are no later discounts to come up.
For our stay this fall, we booked at 499 days out. Our stay is AKL then B2B2B on the Disney Dream then CCV. For the CCV portion, we initially booked at WL because CCV wasn't available to book for cash stays until about 10.5 months out, so we changed from WL to CCV at that point - but the WL room we booked is what we were happy with had there been zero CCV avalability. We watched availability fluctuate over the months since booking -- at times there being zero at both resorts and then it come back. Right now, months out, there are zero rooms at all resorts but one (which only has one very expensive room type available) for the AKL dates of our stay, and more availability across many resorts for the CCV dates. For this stay, while I would love for there to be a room only discount, I am realistic that with the combination of declining WDW discounts in general and SWGE specifically, we are not likely to see a discount for our dates. For our stay our only park visit is
MVMCP so we didn't have to do the "where to get park tickets" math that you will have to do.
Another factor to add to your equation is whether you will want to do the Mickey's Not So Scary Halloween Party [
MNSSHP] during your trip. It is a separate ticket event.
I realize this doesn't answer your question, but hopefully it gives you some things to consider as you make your decision.
SW
There are 15 of us in all including my family, my parents, and 2 of my 3 siblings with their families, my other sibling opted to go on another Royal Caribbean Cruise instead of coming with the rest of the family 
I know - it makes NO sense why anyone would pick a cruise over WDW!! 
