Maybe do a little pre-work - call and find out what's available in the resort that would be your first choice and 2nd choice and what the cost would be. Add in
DDP or not, park tickets, check airfare, etc. And then work out a budget to show him. Don't forget
MVMCP or Candlelight Processional if you're inclined to go. Although this could actually make him more uncomfortable with going - if the cost is too high. But I would think you'd want to find out one way or another...soon. If it is a question of cost - offer to take a lower cost alternative hotel than perhaps you'd like. Try to find discount air (we're flying in and out of Tampa on Southwest because we got tickets for $200/RT/each) which might mean staying longer.
In my case we hadn't been to WDW since 4/04 and this past April we gave up ressies for a
Disney cruise and 5 days at WDW to go visit his parents in CA (recently relocated there) and his brother in Tuscon,AZ all on the same trip (because DH had a conference in AZ which messed up our vacation). We spent way more on that trip on cross country airfare, house rental, 5 star hotel, cars, meals, etc. than we would have on WDW and cruise.
So when looking ahead to 07 and where we might vacation and when.....(trip with DH's family is in the planning stage - all 20 of us - do I have to go??????)..and I realized that we wouldn't have a week to ourselves again - our family for two years.
So I mentioned that I thought we ought to make the time by taking the kids out of school for a few days, that it ought to be special (oldest DD goes to college next Aug) as in Thanksgiving/Christmas and that it ought to be WDW. Unfortunately......he had no recourse since I was such a sport about ditching our WDW plans this year to rebook an extended DHfamily trip in CA & AZ. He owed me! He said "sounds like a good idea", which of course was the "right" answer.
Best of luck.