Last November went with all my kids and their spouses - total of 10 people for 8 days. We had the dining plan and POFQ rooms, 7 day park tickets and with airfare it was about $22,000. I paid about a third of that, the working adults paid their own way. Great holiday, Christmas decor out and we saw the Osborne Family Lights in their last year, but wow. Expensive. The "kids" are 21-32 so no cheap food. We had 3 rooms. Extras were kept to a minimum but I think each room spent another couple of thousand in drinks, tips and shopping. When you convert it to Canadian dollars it's a down payment on a condo!
This summer it will be just DH and one DD, the WDW nut who has worked there in the past and reapplied to the Canada Pavilion this year. 1 room at CS club level, got park hopper tickets for 6 days of the 7 we will be there, in case of free dining. Free DD did happen (we are there Sept4-11) so that saves us something. Room & tickets & dining total $3466.05 plus airfare will be about $600-700 Canadian each. Add on another $2000 for drinks, tips, shopping and so on. Alice will pay her whack so I guess I will be out about C$5000.
Then I lost my mind and booked DD and I in for the Food and Wine 10K in November so that's another $2373 plus airfare and food. Disney addiction is definitely postponing my retirement, lol.