Marandahir
Crown-Forester (he/him)
One major issue with settings is that TSR created a bajillion of them. Then they discovered they were competing against themselves. Putting out a periodic setting book (or licensing one) keeps some interest, but it also keeps it from feeding on itself. As for completely new settings, why bother when you've got a gigantic supply of existing settings under your control?
Incidentally, this is also why we get only a handful of products a year from WotC. Why spend the money to print oodles of books that compete against themselves when they can outsource the filler resources to the DM's Guild and take a cut of each pdf on-demand sale?
3e and 4e may not have had 2e's problem with too many settings, but they definitely followed the problem of too much too fast. Pacing the material out means you can turn out high quality products, playtest a lot and get the crunch and flavour just right, and it means it's a boatload more likely that most tables will purchase your darn books in some capacity (D&D Beyond's partial purchases are a godsend in this way - folks who would have bought the pretty book still buy the book, but folks who wouldn't have been able to afford the whole book every book but want a bit of the crunch from it can buy just that bit and WotC gets a sale).
Consumer data is much more effective these days. Even back in 2e, a lot of the strategy of the time was "throw it at the wall and see what sticks." The ubiquity of the internet, social media, web browsers tracking your searches, companies like Amazon tracking your purchases, it all means that WotC has the tools at their disposal to be extremely smart about how and what and when they publish books, settings or otherwise.* Project Insight isn't about shooting down everyone who might resist HYDRA's new world order, it's about selling us paper and plastic and virtual toys. Crack is cheaper.

I'd say then, WotC's choices could alternatively look conservative or adventurous from an outside POV because we don't have the big data that they do. I personally think that boiling down all smart investments and spenditures to a company acting fiscally conservative is a bit shallow a perspective. In this capitalist system, the company (Hasbro) is responsible to its shareholders, and is trying to make the biggest profit it can for them. Whether that's in a short term turn-around or long-term turn-around depends on what the Board is pushing. Usually it's a mix of both, or erring on the short-term. But short-term vs long-term aren't synonymous with adventurous vs conservative – a short term profit could be linked with an adventurous choice if the company decides to bet big on an untested stock, but it could also be linked with a conservative choice if the company decides to turn out a well-oiled machine rapidly. We can't really pierce the veil of which are conservative vs adventurous choices without the data. We CAN see that WotC are slowing down to turn out long-term products, spending far more time of R&D, and leaning into licensing deals to create stop-gaps between these products. But the products themselves could be considered adventurous if they are untested. You never quite know what the sales will be until the product goes to market. We just have SO much more data these days that by default, any smart company that wants to stay afloat is going to look somewhat conservative in their choices because they're playing a different game than they did 20-30 years ago.
ANY company. Think about baseball. Yes, the ball players are the stars, and their speed and abilities create openings in the game for profound moments, but every professional team now spends an enormous amount of time pre-gaming out the matches and choosing just the right pitchers, fielders, and batting orders to combat what they know from the past pitching and battling profiles of their opponent teams. And then they spend time and energy training those team members to be ready to win against them. All the teams are doing this, so the victories are either in the budget differential between the teams, or else in the margins opened by profoundly transformative players. Hence why the biggest expeditures on ANY professional sports' team are to buy transformative players and in big data research and strategy.
We live in an era where the term conservative just doesn't describe how companies use data anymore.
*Tools too - the technology of the time finally allows for online, easy to use, content-license-included virtual table tops and rules encyclopedias, unlike the incredibly roundabout and difficult to use and financial disasters that were the 4e digital tools. Gods, I loved them, but I would never go back to them from what I use now. And those tools further feed into the consumer data analysis team at Hasbro.