…the peeling and chopping of the squash is the most tedious part…

For winter squash (what the Brits call ‘pumpkin’) I find it easier to roast first, then scoop the squash out. I split lengthwise, scoop out the seeds and the soft bits around the seeds, put in a pan cut side down with 1–2 cm water (enough to cover the cut part) at 350F until the squash ‘gives’ when I poke it with a finger. Take out. Let cool, scoop. The water helps cook plus makes the pan a snap to clean afterward

If you’re making apple/onion/squash soup (or just squash alone) roasting adds a nice smokey note that you don’t get with other methods.

I like the idea of combining with tomatoes and pasta (looks like radiatori works best?). I’ll put some radiatori in my re-order for pasta-from-Puglia we get from delallo.com. Sadly, fresh tomato season has already gone by here.