I had hosted Plaqueimaging.com at Bluehost as a Wordpress.org installation since 2009. I enjoyed the challenge of finding a theme I liked, setting it up with plugins to do what I wanted and learning a bit of HTML/CSS along the way. The flexibility was great - there are plugins to add almost every type feature you could want to your site - Twitter/Facebook/RSS/e-commerce/Youtube.
But recently, as I started blogging more often and adding more features to the old site, the Wordpress plug-in and theme updates just got too frequent - and too nerve-wracking. I never knew if updating the theme or plugins might break something I had spend ages getting to work.
The site load speeds also seemed to be getting slower. Like 8-10 seconds for the front page.
It was very easy to get a vanilla site up within about 45 minutes. I did just that for my father in law. But to move a site across from Wordpress was more difficult.
First I had to convert all my Wordpress tags to categories. this is because Squarespace only imports categories for Wordpress. So then, once I had imported the blog using the blog import feature, I used a Squarespace feature to swap categories into tags.