I would also argue that the "quirkiness" of what the OP is attempting to do that makes it such a difficult edge case is unnecessary too. For example, their simplest example of two executables that generate files that the user has to manually share between two folders is still completely do-able if the author just simplified the execution. If it's really just a game, and nothing more, then they should be able to just make it 1 executable that opens its own sandbox where there are 2 fake executables inside of it that do whatever they need to do to make the game work. There's literally no reason, other than the gimmick and novelty, for this game to have to run as 2 separate executables that actually play and have access to your documents folder (or whatever folder on the drive the "game" happens under).

It reminds me a lot of the uproar on Windows when shortcuts were indistinguishable to an application from the actual folder. When MS changed this so that the end result was the same but the applications were also aware of whether they followed a shortcut or not, there was a bit of outcry because it broke a few apps that relied on the file system not knowing the difference. In other words, these apps built their entire functionality around an unintended bug and then cried foul when that bug was fixed.

In this case, at least, the author just seems upset because they can't continue to create things that are immediately abandoned afterwards. They've become reliant on being able to constantly create new work.