Steam gets this so right - games change price all the time, go on sale etc.
It's the same phenomenon you see with landlords - rental properties go unoccupied for huge periods of time because they believe they'll get a better deal just in the future - with media we've let absurd copyright durations do the same damn thing, and probably at the expense of artists and content creators who I want to support.
However, centralization of the marketplace, even from a publisher standpoint, isn't a Good Thing. Steam's degree of control over the game publishing platform market is pretty pathological from the view of developers.
A better solution from the content creators' standpoint is a marketplace with competitors. In gaming, this doesn't really exist (maybe GoG/Humble?) but in streaming media delivery, it does (Netflix, Hulu, Amazon Video).
Free markets don't promise perfect efficiency in each case. They promise to be reasonably efficient on average. They also don't promise perfect happiness for just one side of the market; they're a means of reaching a compromise between all participants.
What hidden complexity am I missing on the delivery / payment side?
Not speaking of making content free, but making content easily accessible, at a nominal price.
The easily accessible part has been proven solveable, by hobbyists, already.
US movie studios are reasonably good at making movies. They are maybe not so good at translating them into Chinese, figuring out how to market them in China, and distributing through the many channels there (first-run theaters, second-run theaters, VOD, DVD, streaming, and probably more). So they sell distribution rights to other companies.
If you want to replace that, you have to come up with a system that is better both for consumers and producers. Yes, hobbyists have figured out part of what's better for consumers. (Although those technologies are terrible compared with Netflix, so only a part.) But optimizing for one criterion is way easier than optimizing for two or more.
No, that's just easy from a consumer perspective. But it's not simple at all from the business perspective. Making movies and TV is expensive and complicated. Getting them to break even means a lot of careful work to maximize revenue and profit from a variety of revenue streams. It means dealing with a lot of players that are trying to maximize their own revenue and profit.
Things can and will get better. But not by ignoring the essential complexity of the domain.