I go two-three times a year. Why? I hit rides in the winter more when it's not excessively hot, and hit the pool amd the water parks in the summer and less park time. Pretty simple. We have annual passes that we bought with our dvc discount, so basically we pay for the room (which usually we use our points for) airfare, and food. We don't usually eat out at home, so that's vacation money. And in June, we use our points to go elsewhere. Last June we did Disneyland and Hawaii, the year before that we did just Hawaii, year before that and every December we go to South Carolina. This June we are going to South Carolina, next year probably Hawaii, and then the year afted a long SoCal trip.
Last WDW trip didn't cost a lot. For a 9 day trip, it cost $650 for a room at Pop with an AP discount, nothing for $20 for Southwest airfare thanks to frequent flyer miles and a few vouchers, and around $550 for food and a few souveniers. It cost my friend around $1500 for food, airfare, and her pass. Not terrible for either of us I must say. I did get to see the castle all decorated with the ice, which I'd never seen before. If you take the parks slowly and rotate what you do, you'll hit something new every trip, or at least something you haven't done in a while. We did BATB, which I haven't seen in six years, Finding Nemo: The Musical, which I haven't seen in over 2 years, we ate at Boma and Cape May, which I usually don't get to do, I hadn't seen Little Mermaid in a while, and I hadn't stayed at Pop in a long time. In August I will hit the water parks and the pool. We're already talking about going again next January, and we'll do some different stuff. There's somethig to be said for taking in the parks slowly. You'll notice stuff.