I can't remember where I saw this, but I read an interview with one of the head guys at Disney where they asked him if the failure of Tomorrowland, The Lone Ranger, etc. would deter them from making any more films like that. His response was that it wouldn't because they feel it's important to keep trying different things and not just settle for churning out what they know will sell.
I would argue that Tim Burton's Dumbo fits that category because you know it'll be different and probably unrecognizable from the original film. And that's a good thing. If they're going to do all these live action remakes, the best thing they can do is experiment and let each director do their film any way they want to so it won't just be a rehash and there'll be a reason for it to exist. Personally, I thought Tim Burton's Alice In Wonderland was better than the original *ducks*.
Well, I did not see Tim Burton's
Alice in Wonderland remake, but I will remind you (and others) that Walt himself did not seem to think too much of his own take on
Alice in Wonderland. You may remember that he lamented that it did not have heart, and that he believed that was why it was a failure at the box office.
That also reminds me that many Disney films that we call classics today were box office failures in their initial release. Look at
Fantasia, which they are celebrating even today with a 75th anniversary showing at theatres -- which has an iconic image (sorcerer apprentice Mickey) that is now universally recognized. It was a financial disaster. Also
Bambi was a financial failure at the box office, but later became a reference standard for art in animation.
So, first, I want to note that maybe you are not alone in finding the Tim Burton film better than the original, because even Walt himself found the original lacking.
And, second, just because a film like
Tomorrowland does less at the box office than they might have hoped, it could find its audience over time. I liked it, and as a youth director at my church, I noticed that so did most of the students in my program -- and they can be a cynical as anyone else. So, I wish people would change the narrative on
Tomorrowland being a failure. Maybe it was as a percentage of its budget, but it has had an influence, and may continue to do so.