We usually average 3 WDW trips in a 2 year period. With ~ 50 WDW trips under our belts (starting ~ 20 years ago), here are some things that have helped us over the years (in no particular order):
My DH and I each have SWA VISAs, each getting in on the 50,000 RR points offer. That 100,000 got us ~ 8 round trip flights from Indy to Orlando.
I save ANY found money for vacation (birthday $$, rebates, $$ I get for doing my DHs business quarterly/annual tax work). I am very lucky at winning things on the radio

. Anything that I cant use (i.e. local theme park tickets), I sell to friends at a large discount and put the $$ in the found money fund. A few local grocery store pharmacies offer a $25 credit if you transfer a prescription. DH has several Rxs, so I transfer when I can and then use the $25 credit to buy a $25 Disney gift card.
I have a portion of my paycheck automatically transferred to my vacation savings account each payday. I have done this for years and years, so I dont even notice it.
I receive an annual bonus. Half of the bonus goes in the vacation fund and half of it goes into our regular savings account.
Depending on what the current incentive offer is, I use my DISCOVER, SWA VISA or Disney VISA exclusively to rack up rewards to be used for vacation related items. All credit cards are paid in full every month. No exceptions
.ever

. DS is 24 and on his own at grad school. I think one of the most important financial lessons I taught him was this

. It makes you think twice about that impulse purchase.
DVC

. I first toured in 1997 and then again in 1999. After running the numbers a few times (Im an Accountant, I HAVE to do that

), it made sense for our family and travel style. My only regret, why didnt we do it in 1993 on our first family trip

?? We paid for DVC with some $$ from the sale of some property, so we only have the monthly dues (which after all these years, I almost forget about). A few times we have been used as a referral for friends that bought into DVC. That was the easiest $200/sale that I have ever made! We have had years that we have banked points and then been able to treat friends and family to a DVC stay

.
I have had a WDW annual pass probably ~ 10 times over the course of the last 20 years. The DVC discount makes it a great deal. My best 12 month period was getting 4 trips out of one AP. I think I had ~ 35 park days.
The dining plan used to be a great deal for my big eating DH and DS (especially when it was free), but it has totally priced itself out of our budget. We have been using the Tables in Wonderland card (at a discounted price thanks to DVC/AP

). The TIW discounts that we received on our 8 night WDW trip last month more than covered the cost of TIW.
For longer trips or those with extended family, we either place an order with Garden Grocer/We Go Shop or we rent a car for a day or two for an offsite stop at Publix (my FAVORITE grocery store). I add my normal grocery spending to our vacation budget, since we wont be spending that $$ at home while were on vacation.
I love, love, love shopping at WDW. To try and curb those costly shopping trips at World of Disney

, I try to plan a visit to Disneys Character Warehouse at the Orlando Premium Outlet Mall early on in our trip. Several times I will find something at a greatly discounted price that I saw at World of Disney just a few days earlier for full price.
We have been lucky enough to be friends with people who were/are in the Disney College Program and have shared their awesome discount with us. Last year, when I had a big birthday, I was able to plan an impromptu WDW birthday trip with a friend and get our room at a 50% discount and the
Disney Dining Plan at a 60% discount. I already had my AP and I used SWA RR points to fly, so it was a very cheap trip. There is a potential for another trip soon before my AP expires

.
Besides WDW, we love
Disney Cruise Line 
. We just became gold members last month after sailing for the 5th time. The price of cruising with
DCL seems to have skyrocketed (more than doubling in 5 years

), so I dont know when we will be able to cruise again. We cruise with 4 other families (that we met on the DIS cruise boards before sailing in 2009

) and have talked about doing the Alaskan cruise in 2 or 3 years. Hopefully, one of us wins the lottery or DCL offers some great IGT, OGT, VGT rates.
In general, I am a very frugal (or cheap, as my DH says

) person. It pains me to ever pay retail prices, especially for clothing. I want it on sale; have a % off coupon and some cash back promotion too. I grocery shop primarily based upon whats on sale. A few weeks ago my DH asked me to get a lot of berries (strawberries, raspberries, black berries) at the grocery store on my weekly trip. I said I will, if theyre on sale. Looking shocked, he said You only buy them if theyre on sale?? Weve only been married ~ 30 years
.you think hed know me by now! My biggest vacation struggle right now is paid vacation time at work. I used to get ~ 25 days a year. I recently switched jobs and now get only 10 days a year until I have been there for 7 years. There are talks of a change to happen soon. I sure hope so, because it is cramping my WDW plans

.