Here are some possible answers. I suspect they are all in play to a degree, though some less than others.
● Hollywood Is Out of Touch: This is a pretty standard talk radio conservative line. The argument is that Hollywood is run by who-knows-what, and they hate us and our traditions. The problems with this are obvious, however. (1) Hollywood isn’t actually “run” by anyone. Hollywood is whoever has the money to produce films. So any theory that relies on a monolithic Hollywood misunderstands the structure. (2) This doesn’t explain why old Hollywood didn’t do any better. So while some people may be like this, this theory simply doesn't make sense to explain the issue.
● Stories Need Angst: This argument goes that audiences don’t want to see films that are puppies and unicorns, so if you do a holiday fail, it generally needs to be darker. This is why you get stories like Planes, Trains and Automobiles and Jingle All The Way, which are about the negative side of the holiday experience. But negative doesn't sell during the holidays. So few holiday films are made.
I disagree with the angst argument. Good stories need conflict of some sort, i.e. something that the hero must accomplish despite challenges, but those conflicts don’t need to be negative, nor do they need to be presented negatively. One of the things that makes The Wizard of Oz so engaging, for example, is that while Dorothy must overcome various evil hurdles, Dorothy is relentlessly positive and all the other characters feed off her strength. So I don’t accept that this angst argument is true. That said, however, I do firmly believe that a lot of people believe the angst argument, so I can see this motivating Hollywood to avoid more positive holiday portrayals.
● It’s All Been Done Before... By Icons: Hollywood isn’t really concerned about originally, far from it. But every once in a while, an iconic film comes along and you can’t make anything remotely like it without people calling it a rip-off. An example of this would be Star Wars. No one has tried to copy the elements of Star Wars because they know people will be upset. In fact, the first real copy I can think of was Eragon, which was written 35 years later and even then was panned for being “Star Wars with dragons.”
When you look at the stories that dominate the holidays, you see a couple iconic stories that really do eat up large parts of the holidays. Foremost among those, you have the claymation Rudolph the Red Nosed Reindeer, which completely dominates the story of Santa, and you have A Christmas Carol, which completely dominates the idea of repentance which comes with Christmas. What does that leave really? Rudolph encapsulates the “story” of the holiday (apart from the religious aspect) and Christmas Carol dominates the emotional aspect. Between them, that's everything that has meaning about the holiday, and any story you write that touches upon either of those will be seen as little more than a knock-off (the religious aspect is covered by the Nativity Story). That leaves only pieces at the edges, like the shopping experience (Jingle All the Way), and parodies like Bad Santa (parody of A Christmas Carol) or Elf (parody of Rudolph). Indeed, ask yourself what Christmas tale you could tell that doesn’t feel like you are borrowing heavily from one of these icons.
I think there is a lot to this. Anyone doing a Christmas movie will find that the more they strive to include an emotional impact, the more they are accused of copying. That creates a pretty strong incentive to make something else... or just to do a remake of A Christmas Carol.
● Fantasy Won’t Do: Finally, we come to the reason that I think really keeps Hollywood out of the holiday business. Hollywood is about fantasy. They get rich by selling us dreams, stories we would love to witness but which will never happen in our lives. In effect, they are selling “The Vicarious Experience.” But you can’t do that with the holidays because we’ve all lived it.
Think about it this way. When you watch a sport movie, you get to imagine yourself as the sports star you never were who overcomes incredible odds to win the game on the last play in an amazing manner. When you watch action films, you get to dispense justice against criminals and terrorists you can’t touch in real life. When you watch a romance, you are the suave lover with all the right words who makes all the right decisions and in the end wins true love with the ideal mate – people who don’t fart or burp or forget to shower or get drunk watching a ballgame, people who only care about you every waking moment. You love these things because for that brief moment in that film, you get to experience something real life will never give you.
But what do you get out of a holiday film? You get a sense of being with people you love. Got that. You get a sense of happiness as people give you presents. Got that too. The holiday spirit. Ditto. You get a chance to fix relationships that aren’t always grand throughout the year. Yep, got that too. See the problem? There is nothing a film about Christmas can provide you that you can’t already feel yourself. People don't see films that offer them nothing they don't already have. And all this really leaves, again is parodies, like Christmas Vacation or Jingle All the Way, which poke fun at what you've experienced, or the retelling of classic stories. But those things don't sell all that all. So again, it's better to avoid the issue and make a different movie.