These aren't positioned as good-better-best. Rather, each is compromised relative to the others. Neither of the prior two Pencils worked across all iPads, yet Apple kept the original around by making only it compatible with an iPad that post-dated the later-released Pencil. This was especially odd in light of original's bad charging solution. And although the most recent Pencil seems to be positioned as the low-end model, it has a charging port that reflects Apple's newest standard, and which some users of the "high-end" Pencil might also benefit from. The lineup is simply a mess.
Also, "more choices at different price points" really only works where there are clearly different target buyers between the products (e.g., MacBook Air vs. MacBook Pro) or where the differences are sufficiently clear to generate an upsell effect (e.g., people looking at the "starts at" advertised price add features and end up with a higher typical price). Given the relatively minimal core functionality of the various Pencils, the far better decision here would have been to make one great one and price it at a point that makes it an extremely common add-on when purchasing an iPad. Apple hasn't achieved that.