It is a mystery

Yay roast!

That amount of maple syrup is the cranberries-and-sharp-apples amount, so I can see squash coming out a bit sweet. (chorus: depends on the squash! everything depends on the squash!) Dryness can be the dutch oven lid; the tighter the fit, the less dry. (There's at least one cuisine where they use clay to seal pots; that's probably going too far in this application, but it wouldn't hurt.)

It's a very versatile technique. The only thing to watch out for is if the liquid starts with anything able to settle; it will tend to settle and burn. (had a bad experience with popped quinoa that way.)