Our family has what we call "veggie night" a couple times a week, and I am always trying to come up with something the family will love (or atleast like) so that they don't come to hate veggie night. This is my newest creation. I got the idea for using squash in the pasta from seeing Alton Brown use squash to make gnocci (which I have also made and enjoyed several times). My daughter loved it, while my son was very reserved once he saw the spinach in the filling (which you can't even taste, sheesh.) My husband hasn't come home for his dinner break from work yet so his reaction remains to be seen but he loves the frozen cheese ravioli and this tastes a lot like it (only a lot healthier), so I am sure he will love this too.
The seasonings of course should all be adjusted to your taste, these are just the amounts that suited us. The roasting of the squash can be done in advance either the same day or a few days before hand since it needs to cool anyway, or you can use canned pumpkin and skip the roasting step. And actually the ravioli can be done in advance and frozen, This would probably make a great OAMC meal.
I did not include time to roast the squash in prep-time since this is meant to be something you'd do in advance.