The Starter Set seems to be the poorest selling D&D product. So I doubt they’d want to make a new one regularly. And I doubt many people will buy more than one Starer Set, as half the contents only appeal to new players.
I can see them trying to make a better one, designed with feedback from the first and taking into consideration the needs of the current generation. Perhaps a QR code linking to a how-to-play video.
The point of the starter set from a marketing perspective is to have a version of the game that can sit in non-book store focused retail and capture the market that would normally never be exposed to the brand. While it's definitely aimed at new players, its value is advertising before conversion (assuming that the units sit on a shelf and some don't actually get sold).
So creating new art for the box is occasionally going to be a good idea, and creating art specifically for certain outlets to maximize visibility (Target is mostly red and endcap space benefits from contrast) might be a good idea depending on specific metrics and location.
Do I think WoTC does this sort of analysis to increase sales. No. Do I think ASMs at big box retail do it? Yes.
However, the shift of sales from conventional retail to online and specialty sellers makes the liklihood of new versions of box sets very low.
On the matter of new content in each box set:
If the content amounted to three pages of text that could set up a map, an antagonist and some flavor for things, then I'd think it was a good idea. Better still, come up with three or four related adventures, label which one is in the box and put it out there. If the short adventures can be played on their own or as part of the line of four, and each is only 3-5 pages in length with some advice text for the novice DM, you'd sell more stuff.
I know that I can blow through a 3-5 page module in terms of writing in a day. Wouldn't take much to add some editing on the back end and give yourself something to advance sales. Absolutely no one is expecting Tomb of Annihilation in the Starter Set.
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