We used to stay off-site to save money until we found this site. With the info I have been able to gather from this board, we have been able to stay on-site every trip since 1999. I really prefer staying on-site for the convenience.
We live about 7 to 7-1/2 hours north of Orlando, so we are able to leave extra early in the morning and make as few stops as possible and arrive around lunch or a little after. This gives us time to check into our hotel and go to the parks on our day of arrival. With our AP's this year we have made four trips already and will be returning for a long week end at the end of September and eight days at Christmas.
If you decide not to shorten your trip, consider annual passes. We buy three (two adult and one child) it runs in the neighborhood of $1000.00 to $1100.00. The break even point is between seven and eight days in the park.
With the annual pass, you can often get a discount that can be as much as 40% off rack rate on a Disney hotel. You actually don't have to have an annual pass for each person in the party to qualify for the AP discount. One would be sufficient. And you don't actually have to have it when you make the reservation.
The AP rates don't come out until a couple of months in advance, but you might make the ressie and wait to see if one comes up. If there isn't an AP discount for your time frame, you can cancel the ressie and get the deposit until 45 days prior to check-in time. If you go in May, you probably will be able to get the AP discount.
If you are military, DOD, retired military, or retired DOD you can ask for the Shades of Green discount at the Disney deluxe's. Normally, this discount is only good at the Shades of Green (a nice deluxe in its own) but SOG is closed for expansion. If you are government, nurse or teacher, you would qualify for the $129.00 @ Swan/Dolphin. With any of these options, you probably won't need to rent a car and that will save alot of money.
At that time of year, you might also be able to get a code discount for a Disney Deluxe or Moderate for a little around the S/D teach rate per night, maybe another $20-40 per night for a deluxe.
I never knew there were so many ways to save on Disney Properties until I found this board. Another recommendation is to bookmark MouseSavers and go there often. The address is:
http://www.mousesavers.com/ .
For breakfast, you can bring cold cereal or pop-tarts and save the cost of breakfast. There are plenty of other ways to save and still have a great vacation. Also check with
Dreams Unlimited.
One final suggestion, if you are looking at packages, reconsider an ala' carte trip. My experience is that it is almost always cheaper to book everything separate than to buy a package.
I realize that because of distance, you might not be able to return within a year, but it sounds like you would like to make this "a trip of a life-time", but trust me, you will want to go back again.