We have gone every year for the past 5 years...and the one way we can pull this off, is to book our trip wayyy in advance. We usually try to book our trips at least 6 months in advance, this way we can pay a bit off every week. I know the Dining Plan is up for debate on whether you save or not, but for my family it does save us. So we always try to get the Free Dining, we almost always stay at a Value - I would LOVE nothing more than to stay at a Deluxe, but we don't spend much time in the room so for me it doesn't make sense to pay so much more. We will do a moderate if we want the regular dining plan - or we upgrade. We do budget our money for Souvenirs, and try to get things we cannot get elsewhere. I also try to go in off peak times. I don't mind taking my son out of school for a week to go on vacation. As long as I let the office know, they are ok with it. He is in first grade this year....and I already let them know. I know once he gets older it'll be harder to take him out.
One area where I don't really compromise is airfare. We always fly Jetblue since we each get to check a bag for free...I make sure we are paying less than with other airlines including checked bags.
Here is our breakdown for our upcoming trip in November.
10days/9nights at Pop Century for 2 adults, 1 child, 1 infant, 8 day Park tickets with Free QSDP = @2100
Airfare - $797
We do take about $1000 for extras, or in case of an emergency, but we never use it all.