SPOILERS ALSO
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I don't think you're giving the creator enough credit. This game isn't about "winning," it's about dealing with loss and how loss can affect a person in different situations. Everyone dies, but when you have more time with them, it is easier to get closure. I think this game is a beautiful metaphor for COVID, because a lot of people's futures are being but short, either because of death or because the world has changed so dramatically. When August's future with May that she had planned is taken away, it was much harder for her to move on.
I also felt a bit cheated that May died from a brain tumor simply because I didn't want to take a doctor's appointment away from someone else who needs it, but I had to realize that this is a reality: sometimes in life, you try to make all the right decisions, and bad stuff still happens. You can wear a mask, use hand sanitizer, and plan for every eventuality and still get COVID. This is my interpretation of the game, anyway.