I think it all depends on how soon you want to go to WDW and how responsible you are with credit cards. If you can qualify for a Southwest credit card through Chase, meet the minimum spend, and pay off the card every month, you could earn 50,000 points which should be enough for 2 RT tickets (if you pick the cheapest flights, wait for a sale, etc). Regarding "money" for Disney, Chase also sponsors the Disney Visa card. You can occasionally find offers (search online) where, if you open a premier card with a $49 annual fee and meet the sign-up requirements, you get a "free" $200 Disney gift card. If I were doing it (and I did), I'd open one card in my name (with DH as the second person on the account), meet the requirements and get the $200 gift card, collect the rewards points and then close that account and open one in DH's name, with me (you) as the second person on the account. Meet the requirements, pay the card in full each month, get the $200 gift card, but leave this second DIS VISA account open until 11 months. You can charge groceries, gas, and restaurants and earn 2% back, 1% on everything else. Might as well make a little "money" before ordering the rewards points and closing the account (but close it before you pay the $49 fee for the second year). NOW you have "free" airfare on Southwest and $400 or more towards your Disney resort hotel and food.
Make your reservation as "room only" at a Disney VALUE hotel; our "room only" reservation in August, with no discounts, is $135 a night; if you can get a discount or go at a lower cost time of year, you'll pay less than this per night. A Disney resort hotel room will give you free round-trip transportation between MCO and WDW, and you won't have to pay for a rental car or parking fees; just use the Disney bus system. Not my favorite, but it's free if you are onsite (and with the cost of rental cars and now the cost of parking at a Disney park/resort, it's worth it, especially if you can get a discount on the room). At this point, after meeting the minimum spends on the cards (which means charging everything, groceries, gas, restaurants, any bills that don't charge an electronic funds fee, etc), you will be "spending" $49 on each of the Disney credit cards (annual fees) and $5.20 to $11.40 per Southwest ticket. Southwest will give you 2 free suitcases per person; bring breakfast food and snacks from home to save money at WDW. DON"T get a dining plan; you'll do better buying your own food, especially for a short trip. Park tickets will be your biggest expense; check
Undercover Tourist (sign up for the MOusesavers newsletter for a little bit of a discount), Maple Leaf Tickets, etc. If you find someone on Ebay or whatever selling WDW tickets, DON"T DO IT. You have no way of knowing if there are actually days left on these tickets, until you get to WDW, and no recourse if the tickets are crap.
Honestly, if you have the stamina/determination and a year to line up all the credit cards you need to juggle, you could probably squeeze in a short trip for 2 for about $1000. Our seven day trip in August for 2 adults, airfare from Boston, staying 6 nights at a value resort with 6 day base tickets and the
DDP, is costing me about $600 OOP... but I've been planning and juggling this for about 2 years, saving our Disney points (some of which are on the basic card and only at 1%), using our SW miles and two $200 "free" Disney gift cards. It can be done, but it takes time and planning.