I can see them going with two pencils - the one we know today goes iPad 2018 only and connects via Lightning, the new model gains extra features, has an M1 chip, possibly metal construction with colour options, and only charges via a magnetic strip on the side (that "plug it in the bottom" thing is astoundingly bad, almost as bad as charging a mouse via a plug into its underside). They rebrand the current pencil, which is then aimed at schools and consumers. And the new pencil has beefed up specs (increased pressure sensitivity etc) and features aimed at power users (buttons on the side that serve as tool modifiers, or an erase tool on the back end - I suspect they will likely demonstrate this working with Photoshop or Gemini). Plenty of people are doing professional level illustration work on the iPad as it is, I can see the new Pencil being aimed more at them.
Along those lines, I think there will be a price differential between the Pencil and the new one (Apple Pencil Pro? Apple Pen?). I would love to think they drop the Pencil down to $79, but I think it's more likely it will remain at $100 and the new one will simply be more expensive.
I think we're beginning to see the iPads diverging - the stock iPad with the regular pencil will be for everyone, whereas the Pro (with USB-C and lord knows what else in iOS 13) will be positioned towards power users, "pro-sumers" and the like.