I remember our first trip in 2008. For the four of us(2 adults and 2 kids), it was less than 2k. That was staying at the Seralago for 6 nights, 2 Halloween parties and 5 day single park tickets. That also included gas and the off site food for the week.
I don't recall how much the actual tickets were but I doubt we could make a trip like that for that price now. And don't even get me started on how empty the parks seemed that trip...
I had my family trip in 2008. It was about my 35th trip there, but, the first with the entire family. My girl friend, myself, my two daughters and their husbands, three grandchildren, my sister and her son. I rented a 6 bedroom villa just a mile from the entrance, paid for the transportation (both private vehicle and round trip Airfare from Vermont for 7 people, rented two additional cars and purchased 7 day non-expiring (at the time), single park tickets for 9 people.
We ate a couple of meals on site, mostly lunch, but, we did to the
Hoop-
Dee-
Doo Revue , but, each family paid for their own meals. With the villa, we were able to have a few meals at the villa. The villa had a private enclosed full size pool and Jacuzzi. Many meals we just ate at some of the many restaurants along 192. Sometimes we had separate checks and sometimes I bought for everyone. For me it was the most extravagant vacation I ever took and financed. It came to just over $7000.00. Can you imagine how much that would have cost if we had stayed onsite. The other plus was that we only spent 4 days in the parks at WDW. The other three were just side trips to the Kennedy Space Center so the kids could see what all the talk was about, went to a few of the tourist traps in the Kissimmee area and even managed a day of nothing or more correctly, whatever each family wanted to do. That left everyone with another three days that could be used whenever they wanted to. Everyone used those three days eventually a few years later. It was the best (albeit the most expensive) trip I ever made there.
That said I went by myself a couple of years ago, granted it was just me and by then I lived in NC which is a day trip to WDW with Park Hoppers, but I spent about $1600.00 for everything. Golden Corral helped keep the food cost down to a manageable number.