I now understand why canned filling is practically ubiquitous. Dealing with pumpkins is quite a chore. The goal, at least for pie making, is to end up with a puree. Kit did the honors of scooping out the insides and cleaning them. Even once they've been roasted, the oversized gourds don't want to blend.
Sure, if I had a BlendTec, the answer to "Will it blend?" would be "Yes." With a Cuisinart, the answer is "Slowly and painfully." The secret, such as I can tell, is to use a good drizzle of oil to help it along. Not like you're making an emulsion (pumpkin aoili?) but just to lubricate the chunks and get them to swirl around.
Now the pie's out on the countertop, cooling. It's the first time I've ever made a pumpkin pie from scratch. (Well, okay, store-bought crust. So never mind.) We'll see tomorrow if the result is worth the effort expended.