@Andrea_R - Yes, definitely a good match for a fairly substantial proportion of site owners, $50 wouldn't go too far if you had to hire WordPress expertise to iron out the sort of nit-picky problems that crop up from time to time and, yes, the support included with most webhosting doesn't go too far.

@Ryan Hellyer - Yeah, that pretty much hits the nail on the head: looks good for a relatively low-traffic site that needs above-average uptime and responsiveness but the jump from $49 to $199 is a bit of a trap, especially as the type of site owners who feel the need for special hand-holding would, presumably, find it difficult to move a suddenly active site elsewhere but, of course, most sites will never encounter that problem.

Much as I love WordPress, I quite often come across situations in which WordPress is not strictly necessary and, if a business needs a simple, reliable Web presence, I often point them in the direction of SquareSpace, mainly because I know that the included support will include all aspects of the CMS, whereas mainstream hosts are reluctant to cover all aspects of WordPress.

WordPress-specific services seem, thus far, to be a lot more expensive but I would certainly recommend Page.ly or WP Engine if the person asking was already comfortable with the WordPress dashboard, loved a particular WordPress theme or needed functionality that only a WordPress plugin could provide.