We fly out of Seattle, and usually manage to get fares in the low to mid $300s. I like to get early morning flights so I can be arriving at MCO by 5pm ish
I watch flights on Kayak.com too.
Booking WDW hotels, you have to click on the link under Special Offers. There are different Promos released all the time. You can also look on Mousesavers.com Do a search on their site for Historical discounts. You can see when past discounts were released, and what they were.
If you just go on the WDW web site and use regular link it will quote rack rate.
If you have AAA you can get up to a 20% room only discount depending on level of resort.
Disney can release discounts of 20 - 25% on values, 30% on moderates, and 35% on deluxe resorts for room only. They also release packages that include tickets and dining plan.
You have to do the Disney Math to figure out which will be the best discount for your family.
Some do a room only discount, then buy tickets from a site like
Undercover Tourist. I have done this in the past. They sell WDW tickets with a bit of a discount and they send you real tickets, tax is included in posted price, and no shipping fee. So be sure you compare apples to apples. WDW web site doesn't show tax till check out.
Personally, if it's your first trip or 2 i think its a good idea to use a Disney Authorized Vacation Planner. They make sure you are getting the best prices, and are helpful planning too.