And even if that's a non-issue, what I'm talking about is a bit more robust solution - providing the user with some basic tools (like doing markdown/haml pages) right off the bat without any additional hacking.
On top of that, installing dropbox-cli as simple as it might be, is not simple enough and requires access to the shell (that not everyone might have), running a daemon, and it's not super secure (you need to store your root password, no?). My idea is that whenever you install a drophost, you get a new folder in your dropbox with the name of your host (i.e. /dropbox/drophost/mydomain.com/) which is simple to navigate and maintain multiple sites.