Hi!
I didn't read through the whole thread but have an idea that it is different for everyone.
I can only tell you why WE can afford to go to WDW so many times.
In a nutshell -
Priorities, circumstances, and sacrifices.
Priorities:
We will chose travel over eating out, clothes, cars, and most importantly a HOUSE.
Circumstances:
I have a very low paying job but it affords us medical insurance, subsidized housing, and flexible hours. DH has been lucky in the last 18 months in a job he enjoys and opportunites for salary increases. We are VERY lucky in our circumstances that we have lower financial obligations than most folks, have more disposal income, and can use more of it on travel.
Sacrifices:
One of our big sacrifices is house ownership. I get subsidized housing with my job but no matter what we don't own it and it is an apartment not a house. We thought about getting a house anyways. But the costs of such are too prohibitive. The annual real estate taxes alone on any house within 50 miles of where we work would be MORE than what I would pay on an apartment in my building even if we had to pay the full rent. We decided that that if we bought a house, our quality of life in terms of travel and financial flexibility and savings would suffer greatly. So, it is a sacrifice we have made with our eyes wide open. Bringing everything back to priorites...