In reply to Scott.

"Has Matt ever, from the point of view of a non-techie, compared the experience building a website with open source WordPress to building a website using Squarespace?"

Thanks for raising this, I have and I definitely think it's important for more people in the WP community to try the same. If there is a specific type of user you think would be valuable for me to learn more about I'm happy to video or screen share in with you running a test.