Everyone's family is different. I don't think most of us could easily compare our situation to someone else's. Family size, priorities and salaries differ and that needs to be taken into account when you see someone with 20 trips to deluxe resorts listed in their sig. So does amount of time/travel etc. needed for a trip. It's going to cost more for someone from CA to go to WDW than it is for someone on the east coast.
My family consists of 2 adults in their early 30's (okay, I'm 29 but close enough lol) who have no children, no plans for children, and
average salaries for our area BUT combined with
extremely low housing costs for our area (due pretty much to luck). We don't buy a lot of unnecessary things during a given year, we rarely dine out, we rarely buy new clothes, or media. We drive a sensible car that gets decent gas mileage. We don't drown ourselves in bills and debt. Our only responsiblity is taking care of our two dogs and they are both happy and healthy and thus far we haven't had any astronomical bills for their vet care. We also save change and all our various refunds (tax refund, transportation reimbursement from work etc.)
So, our living situation and frugality in our day to day life allows us to be able to take vacations a few times a year. Vacations are a priority. We're both lucky to have flexible jobs that let us take time off whenever we want and not worry about it too much. While I get 2.5 weeks paid vacation (only been at my job for a little under a year), my boyfriend gets 4 weeks (he's been at his 5 years). I also get a weekday off every other week paid as part of a flex time program at my job. So we can look for deals, travel in value season etc. I can't imagine ever traveling in peak season and paying those crazy prices. I only travel in regular season for events such as the flower show or MNSSHP etc.
We also live on the east coast. We are able to fly to FL pretty cheap if we look for airfare deals. My flight home from FL a few weeks ago cost me $55 per person. I forget what the flight down cost, it was slightly more but not horrendous.
We use annual passes because we prefer to go for long weekends (3 or 4 nights usually, sometimes 5) instead of big 10 day trips all at once. That we we can go down a few times a year. The AP gets us significant discounts on rooms at deluxes and okay discounts on rooms at mods and values. It also gets us discounts on other things while we are there. Our APs this year were my birthday gift from my parents (mine) and my birthday gift to him (his).
We never pay rack rate for rooms. If we can't get a good deal on a deluxe,. we'll downgrade, I have nothing against the values. When we are there, we eat cheap, neither of us have big appetites. 3 full meals a day would kill us.
so we eat one sit down and quick serve for the rest. We don't eat a lot of snacks but we also don't stick to a crazy budget either. If we want a cookie, we get a cookie. We also don't buy a lot of souveniers when we are there.
The only really frivoulous thing I will not give up on a WDW trip is towncar service to and from the airport. But at $95 round trip, it's usually cheaper than a cab and makes the start/end of my trip so much nicer. But other than that, when we are there, we don't spend a lot of $$.
So let's review : dual income, no kids, low cost of living compared to salary, frugal day to day living, don't spend on stuff we don't need at home, travel is a priority, live in an area where airfare is not too bad, AP holders who get good discounts and are flexible to travel in low cost season.
That's how we go to WDW twice a year (or more if we don't do any local long weekends around here...we do like other places...but, for the record, a long weekend in a nice B&B in the mountains of NH during fall foliage costs as much if not more than WDW...so there you go...)
My advice to the OP is try to travel off season, look for airfare deals, consider an AP for at least one member of your family if you can get a discounted room, don't rent a car onsite and don't feel like you need to eat at every character meal on the planet to have a good time.
