OK you have a whole year, right?
Work it so everything is prepaid.
Keep your fingers crossed for
free dining, so he can't gripe about the price of food--that's a huge expense. (Plan B: if you don't get free dining, book the
DDP anyway, so the wallet isn't coming out for meals.)
Pay off your room and park tickets ahead of time. That way he won't feel the pinch.
For every event from now till your trip, give the each other and the kids Disney gift cards. Christmas, birthdays, Mother's Day, you name it. That way, spending money is all taken care of.
Keep an eye on air fares. I booked ours in January for our trip in 2 weeks, flying Jetblue. I just checked our flights-- the total price was $1220 when I booked and it's now over $2700. Check Kayak.com every single day so that you know what you could be paying for the flights you want, and jump when they go down. I saved $250 on flights by booking on the one day when each ticket went down by $50; they bounced back up the very next day.
The stop talking about it, just do it. Don't give him any reason to worry about it; answer his concerns with "Don't sweat it, honey. I've got it all taken care of."
As far as rooms go, here are the options for a family of 5, pretty much in order from cheapest:
- a Murphy Bed room at POR
- Family suite at All Star Music
- two hopefully-connecting rooms at a value
- Suite at Art of Animation
- Cabin at Fort Wilderness
- Deluxe room in Garden Wing at Contemporary
- Deluxe room at Beach Club, Yacht Club or Boardwalk
- Deluxe room at Poly
- Deluxe room at Grand Floridian.
One other option you'll want to take a look at: Call the Dolphin and ask about the teacher's discount for a Deluxe Alcove room. They sleep 6. (Of course, that kills the idea of the DDP.) It was my plan B before I got a great PIN in 2012-- it cost about as much as a Disney Moderate, but for a Deluxe just a few minutes from Epcot.
The reality is that a trip to WDW, particularly for a family of 5, can be very expensive. I can understand his worry. But if you want to make it happen with minimal family drama, find ways to do it without making him worry.