We treat winter squash (we like Kabocha especially) by cutting and roasting, Jennie, but we have found that by cutting in half, putting the seeds out for the birds, and microwaving the halves or quarters, we get it cooked without the use of the oven.
(The seeds are used in recipes too).

There are several types of pumpkin. A sweeter, less fibrous type is best; ED Smith and several other canned pumpkins use this type. Look in your seed catalogues for these sweet, creamy types.
The typical "Halloween" type is more fibrous and has a stronger odor; they make poorly flavored pies with poor texture.

The good ones are generally smaller, and have names like "small sugar pumpkin" and "New England Pie pumpkin." "Autumn Gold" and "Baby Pam" are good, and there are others.