Well Disney is never cheap but we maximise our $$ by:
1/
Fly from the US - we drive from Toronto to Buffalo. Our lowest round-trip fare was late September 2001 at C$110 each including tax. We leave tomorrow at C$182 inclusive. Airfares can change hourly - I check multiple sites again and again every day.
2/
Always fly the same airline. We always fly Continental or partner Northwest. Every four or five trips gives enough frequent flier miles for a free trip - for free trips we fly from Toronto as it is the same number of miles as Buffalo. We use the free trip for a more expensive ticket such as
Disneyland or March Break.
3/
The Annual Pass - a large expense once a year but then so much is "free". By Labour Day we will have spent 45 nights in Orlando in the last 12 months - less than U$10/day.
4/
Due to insufficient vacation days we have to make use of weekends and long weekends to supplement our addiction. This does however allow us to experience "magic" that we would otherwise miss such as Flower & Garden, Food & Wine, Halloween, etc. Weekends are also carry-on only to minimise airport time. Fly in late on the Friday night - leave late on the Monday.
5/
Cheap hotels. If all else fails there is always the Comfort Inn Palm Parkway at U$33. I often book it as soon as the air tickets are confirmed in case we cannot get a deal elsewhere. Other options can include Priceline, Marriott deals (our "normal" hotel outside WDW), AP rates. Keep checking - if the price goes down cancel and rebook.
6/
Cheap car rental - no prizes for being loyal here. We usually use National as they have been cheapest for some time with the Disney Club discount and a free day. A compact is cheapest so that is what we take. The Emerald Choice program allows us to just get in a car and drive off - less than an hour from touchdown to the Adventurer's Club even with the toll-free route. This next visit is AVIS as they were U$30 cheaper and that is one night's hotel! If all else fails try Priceline for silly money - it might be accepted. Keep checking - the price can go down. If so cancel and rebook.
7/
Eat offsite - we frequent Goodings at the Crossroads but also the three local Publix. A supermarket supplemented by a buffet at about 2pm can be very filling for U$20/day. Akershus and Trails End are cheap buffets. AP lunch discounts Monday to Friday also help. Leaves more money for Boma or Macaroni Grill later in the week
Hope some of this is helpful to others - certainly keep repricing everything. You will not be notified if the price of something is less than your reservation! Just rebook it and cancel your original (in that order of course) - never book anything non-cancelable except ridiculous priceline deals