I don't think it is a dumb question at all! When I 1st visited these boards last fall I was planning our 1st trip to WDW ever & there was no return trip in our future. Now all you have to do is look at my signature line to see I am heading back next month & again next year. I have found many ways to help save for these trips.
1. DH can, fortunately, work overtime when we wants, so he does this occasionally. We determine the amount he was paid for that overtime & keep it in a separate bank account.
2. I set aside a certain amount each month or week to purchase D$, this year we did $50 per month. I can save up the $50 in lots of ways--can & bottle return from soda, set aside $$ saved from using coupons & other grocery store cards, don't go out to eat as often as before--we got out about 1X per week instead of 2-3 like before.
3. Save change in a big container & watch it grow! Also, I rarely use change to pay for items, I would rather break a bill & then put the change in the jar---it makes a difference
4. Rewards programs can help, even though they seem slower than ever before. We have accumulated $175 in RFC GCs, over $350 in D$, phone cards, GCs to give to neighbors who are taking care of our house, etc..... They have really helped to pay off some of the cost.
5. Book your vacation yourself...check out mousesavers.com for some great deals on resorts..we are staying on property (@ the ASMo) for $55/night inc. tax. Can't beat that price for the Disney **magic**! We also purchased the Disney Club card for the discounts on DStore merchandise, park hoppers and annual passes. Sometimes you can get discounted rates with this membership too. If you drive, there are also benefits the card offers for rental vehicles. Plus you get discounts in some restaurants/attractions in our homtown, so this is definitely worth it! Check out travel sites like Orbitz, travelocity or expedia for very low airfares.
6. Talk about it with your family & see what they are willing to do to help make the Disney dream a reality. For us, it was changing a little in the restaurant area, eating out a little less, & having DH work a little bit of OT. Also, we give DS his "allowance" in D$ . Now we respond when asked what gifts we would like (from relatives/close friends who are buying b-day/anniv. gifts for us)--that we would just like D$ & everyone is more than happy to do so--they think it is very cool.
Sorry to be so long & HTH!