There are two that stand out. Both were off season which helped and having AP's and ff miles were key to going "cheap"!
April, 2005, we had AP's so that expense was already bought and paid for earlier in the year.
We got an AP rate of around $79 a night for POR.
We had frequent flyer miles for three of our four airfare tickets.
We only stayed 6 nights (our shortest trip ever to WDW, we normally stay ten nights or even longer)
We only did a two full serve meals and since dd was under ten she was eating for cheap.
All total, I believe the trip was around $1200.
Three years later, we did a similar trip staying at ASMU on an AP rate, ff miles all the way around and only a couple of full serve meals that were discounted due to having the DDE card. I think that trip we shelled out less than $1000 total. Free airfare and tickets that were already paid for and staying at a value, off season with an AP rate (and again, only six nights) all made it possible.
Wow, I sort of depressed myself when I look back at how much cheaper it used to be! Dh no longer travels for business so our frequent flyer miles days are over, the kids are both teenagers so not eating for cheap, everything has gone up at WDW and my days of getting the four of us there for our ten night trips for much under $6,000 with airfare are over. Which is why we go less than we used to (still go every year but not multiple times like we used to) and will probably not go for a couple of years after this October's trip. Its gotten to expensive, we've been so many times and there are many other things I want to see. We'll be back and we'll always love it, but its hard to justify (for me personally) when I know what I used to pay vs. what I pay now. And our income has gone down which makes it even crazier!
I think that is how I got hooked on Disney: buy AP's, get the discounts, use dh's ff miles and go off season (which I can no longer do since my kids are no longer on year round scheduule at school).