I know the "SJ wouldn't have allowed this" trope is overplayed, but this is one example of where it makes perfect sense when you think back to his Pro/Consumer chart for the Mac. In the name of profit & at the expense of the user/customer experience, they've mucked the iPad line up so much that even I as an Apple fan, iPad owner, and MacRumors reader need a damn features matrix to keep track of the lineup.
If any of my family members (who are all users of iPhones, Apple Watches, a Mac or iPad here or there) went into an Apple Store to buy an iPad, they would need to have an employee sit down with them and walk them through all of the nuances and different Pencil versions and different screen technologies and charging ports and adapters and the 9th and 10th gen being both called just "iPad" and Stage Manager's different forms (or absence) depending on the model and yada yada. The end result is that they would likely either need to take a decent amount of time understanding the differences, or they'd end up just picking one and not fully understanding the differences-- the latter of which could result in buyer's remorse if they later learn about one of the differences (eg: iPad gen 10 and not being compatible with Apple Pencil 2, should they decide they want an Apple Pencil some time after purchase).
It would be one thing if there were many easily-distinguishable SKUs at different price points for the sake of providing choice to the customer. But in this case, it's very clearly done to function as a confusing pricing ladder to push upgrades on low-info consumers that aren't reading MacRumors to understand product differences. Implementing that at the expense of the customer experience cheapens the brand, IMO, and that's something SJ understood.
You can only bean count so much before you turn customers off. And sure, maybe this individually isn't something to cry APPLE IS DOOMED over. Their record profits certainly indicate it's working in that regard. My fear with each one of these bean counter decisions is that the company is now fully under the control of the spreadsheet warriors at the expense of those truly committed to "surprise and delight" and the customer experience that Apple has built its brand on.
EDIT: I should also point out, it's especially egregious that this is being done with the iPad lineup, considering the iPad is positioned by Apple to be the mass-consumer, PC-replacement device of the future. If anything, given this, it should be the simplest product lineup they offer.