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I think it depends on the squash you use. Sure, buying a cheap pie pumpkin or butternut squash at the store might not taste that much better, but a home-grown squash or good local squash can far exceed the flavor of canned pumpkin. As usual, a lot of cooking is about using fresh, good quality ingredients.
I hear what you're saying, but I also hear, "no, just do even more work!" Haha. As it is, baking a single pie is already more expensive than a single store bought pie, and the people I'm pawning my leftovers off to don't seem to know the difference.
On top of that, I live in a high rise in the middle of the city, so home-grown squash is impossible (I barely have space for a few window sill herbs), and anything "local" is going to be even more expensive. Just not worth it to me so I can have a few slices of pie.
yeah, that makes sense in your context - canned squash isn't so bad, definitely not worth making from scratch.
I'm in a suburb where I have grown squash in my compost bin and gotten a harvest that lasted me a whole year, and that squash was some of the tastiest and had the most colorful of any squash I've had. The squash was also essentially free, a waste product, and in that context it seemed worth it (at least in some sense). However, it does take time and planning and a lot more work, and as you're saying depending on who you're baking for they may not appreciate it.