HarryT, JSWolf, I am not sure why you feel the need to protect users from making their own informed risk analysis. I prefer to make the options clear and let the user decide!
In the long run, you are only encouraging people to not think for themselves, which is the true cause of most errors.

Expressing your own personal comfort zone as The One Single Option, does nothing whatsoever other than confuse people.
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BetterRed -- calibre will respawn itself on top of the initial process, so the script will never proceed to the next command until calibre is
properly closed.
As for scripting Dropbox, they have a python script which interacts via unix sockets with Dropbox and allows you to issue a "dropbox.py [start|stop|status]" command. But I don't believe there is a Windows equivalent.