After years of maintaining and hosting my own WordPress and Drupal sites myself, last year I decided to give WordPress.com a trial run for one of my websites. I opted to subscribe to WP's Premium plan over their Business plan. The initial quantity of content for my website was low and I could not justify the higher cost of the Business plan for this site.
Overall, my experience with WordPress.com has been pleasing. While it may be cheaper to host and manage your own website (WordPress is available as free open source software), there is definitely less hassle with letting WordPress the service do the heavy lifting for you. I can see a day coming where I host all my WordPress sites on WordPress.com.