I've tended to shy away from managed hosting quite a while now. I've been happily running a VPS for several years now and although it is more expensive than any of the managed hosts, I have complete freedom to host as many WordPress sites as needed (5 currently) without buying any addons or etc.

I don't need to worry about managing the server since that is done by the host.

I've been tempted to move to WordPress.com but the fact that I can't monetise the sites is a damper. Not to mention that I won't be able to install my plugins there :)