My wife is a Disney person. I knew it when we married. Hell, I knew it before we married. She was poor, barely making it, even using payday loans and having unpaid credit card debt, but she had annual passes to Disney. When we got serious, I helped her get her money under control. She then moved in with me, removing her biggest bill (rent), and the first priority she had was getting me an annual pass. I refused to get one, so she spent her new "extra" income on getting me a pass. That way we could all go together. It was still her money, at that point, so I had no say. She paid her part of everything else. Now that we're married, it is coming out of our money. It's $1,754.40 a year. It's a non-negotiable. We do go enough to make up for it. A lot of the times we go is when she has family down and they go to the parks. Her whole family is a Disney family. If we stay down there, we usually stay off property. My mom owns a timeshare--yes, I am surrounded by people who make bad decisions--and we can stay on that property for as low as $30 a night at times. Even when it's more expensive, it's way cheaper than anything else.
Funny part about vastly expensive things like Disney is that once you've spent the money, you're going to tell everyone "I had the time of my life." No one wants to feel like they've been hustled and with the ads showing everyone with a huge smile on their face, I honestly believe that people force themselves to think that they had a good time.
Everyone having a good time at Disney is a lie. One of our favorite activities, when it's too crowded to do much of anything, is to walk around and people watch. My wife and I have a game we call "not having a magical time" where we identify miserable people and pretend the "magical time police" are going to rush in and remove them from the parks. Adults are 2 points, teens are 1 point, and kids are 3 points. We set the point system up long ago, when we assumed the kids would be happiest and the teens would be too cool to have fun. It's not true, the kids have much less patience for the crowds, lines, and demands of moving around the park. They are usually the easiest miserable people to find.
If we find that we're not having a magical time, we escort ourselves out. With annual passes, we can go back another time. We're usually fine with most stuff, even normal level crowds. It is when they break out the tape and split the walks into coming/going sides and have members out to crowd control the streets (usually at capacity level) when we're done. Those days, it can take over an two hours to get out of the park, if you're near the back, when you decide you're done.