John Lasseter, who was running Pixar and Disney animation at the time, thought it was the movie that killed traditional animation at Disney. A Winnie the Pooh show was never going to be a monster hit. Disney has different expectations for different movies. They considered "A Goofy Movie" successful with a total gross of $36 million, as it was based on a Disney sidekick character.
Princess and the Frog was supposed to be one of the tentpole franchises, and Tiana was supposed to be up there with Ariel, Snow White, etc.
Princess and the Frog didn't fail because it had a black lead. The story was convoluted, it didn't have an earworm song like "Let it go" or "Colors of the Wind," and there wasn't a strong sidekick character, although I kind of liked the firefly.
Disney had been dithering on traditional animation for a while, and Princess and the Frog was a test case to see if it was still viable.
Most of what is called traditional animation now is done on a computer, anyway.
Wasn’t Winnie the Pooh very iconic, though, especially given his constant merchandising and being one of the few characters to have a perfect attendance record in Kingdom Hearts or close to that? I’m pretty sure it would have at least been a decent hit at the box office without The Deathly Hallows Part 2.
And yeah, from what I gather, it was convoluted (though I’d argue it’s less convoluted than with Frozen especially after the whole “Hans” business. And quite frankly, I was not fond of that plot twist considering just how far out of left field it was, never given ANY foreshadowing. It looked like it was taken straight out of Metal Gear Solid 2: Sons of Liberty.). If there’s any consolation to P&TF, at least it treated marriage and traditional femininity in a positive light (not counting sequels, I think the last film to actually treat marriage as a positive was The Little Mermaid, as starting with Beauty and the Beast, they tended to demonize marriage as a woman’s worst nightmare thanks largely to that hack Linda Woolverton, and IF they ever decide to have a character marry, it’s strictly within DTV sequels. And as far as traditional femininity, that Charlotte lady was depicted in a very positive light and was very traditionally feminine, clearly being allied with Tiana and being her best friend. Contrast that with, say, the triplets from Beauty and the Beast. They’re the closest to girls who are traditionally feminine and actually support traditional marriage, and the film demeans them by depicting them as dumb blondes and even had as their official name “the bimbettes”, obviously trying to list them as bimbos just for even supporting traditional marriage and being traditionally feminine.).