We are from Waukesha. Single parent with 3 children under 6. We usually go twice a year. One 10-14 day trip in Oct/Nov and then one 4 dayish trip in winter or early spring. We drove once - no thanks! We always fly. Yes its more expensive but I value my time and sanity more! Usually I am flexiable on dates.
I almost always fly Midwest Express - great service and direct flights. I also did Sun Country a few years back - they did offer good service and some great prices before dropping service.
I keep an eye on airfare deals and thats when we go. I spend more in the fall to secure "about" the time period I want. The other trip is always only based on when I come across a great air deal. Once we went over labor day, once a month after our big trip, once the week after presidents week. So it really varies. Once we actually skipped the second trip cause I couldn't find a good enough deal. Another time I found a great deal on a Sunday nite and we left the next tuesday for 4 nights. Usually buy annual passes every other year getting two big trips on each and then skipping 10 months.
I always rent a car - I do emerald aisle at National. Again the convenience is fantastic. One long bad experience with alamo and that did it. I check the rates every weekish or so and watch for any deals. I'm pretty comfortable with the prices I've gotten.
People who don't know me well assume I spend a fortune since I do Disney often - but in reality I dont. My friends know I watch the specials and try and work within that to get the most bang for my buck. Since we do go frequently I don't really spend alot on soveniers. Last trip my boys got haircuts at magic kindgom and they were happy as clams to get long roles of stickers for sitting still!
I have been doing Disney long before I had the children so it was just natural to keep doing it when they came along.
For lodging
DVC is just cost effective for us. Accomodations are great and price is right.
I guess I just am flexible and watch the specials but at the same time I am willing to pay for conveniences that make my life easier traveling with children.