We manage an average of three trips a year to WDW.
DH and I both work in the I/T field, and make a decent living. I also have a p/t job and my check from that is direct deposited into a savings account, so I never see it. But then it is there when I want to take a vacation

DH also picks up freelance work here and there from two companies he used to work for, and that money gets put away as well.
We pay all of our credit cards immediately, so no wasted money in interest. I also refuse to carry any card with an annual fee. I got the new Disney Visa and we've been using that exclusively in order to rack up points for Disney Reward DOllars.
We're "almost" empty nesters. We chose to have only one child, and he is 17, and will graduate high school in June '04. He has learned a trade, and won't be going to college, so we don't have that to worry about.
We also bought
DVC in 1998 and then added on again this year, so many of our trips require much less out of pocket expense, and we've been able to treat some family members to stay with us who might not have been able to go otherwise

.
We aren't afraid to splurge on special things, but we also bargain shop--I pretty much won't buy clothes and housewares that aren't on sale. I like to shop at Kohl's and Saks Off 5th, brand and designer names at major discounts!
I'm not afraid to ask for things. This year we've scored free tickets to three concerts (Rush, 3 Doors Down, and Nickelback) and a Broadway show (The Graduate) by listening to the radio and showing up where the "Prize Patrol" is handing stuff out, and simply asking nicely "what else they have" when they try to hand us a free t-shirt or sports bottle. Cuts back on the entertainment budget when you get freebies! (We've also gotten a bunch of free CD's and things like that

)
I love getting a facial, but don't want to spend the money for one every month. The spa that I go to for them offered a free "learn to give yourself a facial" class. I signed up myself and a friend. I knew they were doing it hoping to sell a bunch of stuff, but I already use their line and my friend is into holistic stuff and makes most of her own. So we went and learned how to give ourselves facials. We didn't ahve to buy anything (she didn't, I bought somehting I was running low on anyhow) plus we both left with a bag of samples
Somehow DH and I are always getting calls to be on "advisory panels" and things like that. We have to go to a place near our house and watch a movie, view carpet and upholstery samples for a car line, or something those lines, and then give our oprinion. For between one and three hours time, we get between $50 and $200! Wee can usually do this four times a year!
I have extra taken out of my paycheck for federal taxes every pay period, and then know I'm going to have a large check every year right about the time the bill for our February WDW trip hits
We've also been creative in leveraging our assets, borrowing at very low interest rates to obtain cash to purchase assets with a very high return on investment, and then liquidating those at the "right time". Then we paid back the loan, and pocketed a nice chunk of change, we've done this several times now. That money all went into a special account, and we recently used it to buy a house about twenty minutes from WDW--and we'll be able to watch the nightly fireworks from our home everynight

It will be a vacation home for now, but will eventually be our retirement home.
Anne