This is a fascinating exercise. Check out this from Matthew White, creator of alternate history maps:
What is the most fragmented that North America could have been? There are several plausible scenarios (some based on different patterns of settlement from Europe, others on different fracture lines) but I chose 1787 as the point of divergence from real history. In this alternate reality, the westward expansion of the Anglo-American people proceeded pretty much as it did in our reality, but the United States government just couldn’t keep up. Every national identity crisis resolved itself in favor of the separatists instead.
What you wind up with is seventeen or eighteen independent nations where America and Canada are today, and he provides a timeline that shows how, in this other version of reality, things wound up the way they did. Nice. Read and see the whole thing here.