We've discussed this before, but it bears repeating. In my opinion, the only way to cook a winter squash is to roast it whole in the oven. Unless we're talking about delicata which slices quite easily, just stab that big toughie a few times with a sharp knife (to keep him from exploding in the oven), put him in a baking dish (to catch any juices), and roast at 375 for about an hour or until a knife slips in easily. (It totally depends on the size of your squash.)
Once you've let him cool a bit, that previously impenetrable skin slips off like paper, the seeds and stringy bits just scrape right off, and the rich flesh is ready for however you want to use it. If you pop it in the blender you'll have some pumpkin puree with not much more effort than opening a can, but with much less packaging and processing. (That said, I think I am on my eighth can of pumpkin puree for the season, and Thanksgiving is still more than a week away. We just do the best we can, right?)
My pal and I were recently discussing recipe deal breakers. She puts the breaks on any recipe that calls for less than a can of pumpkin. I stop reading when the author tells me to dice any sort of winter squash. (Or it might have been the reverse. We seem to be pretty much in accord when it comes to fussy pumpkin recipes.) Today I am thankful for my food-loving pals of both the internet and real-life variety, and especially the cross-over sort. It's so nice to have people like you to talk to. Thanks for listening and sharing and for all your constant inspiration. What would I cook without you!?