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jimrandomh comments on Items to Have In Case of Emergency...Maybe. - Less Wrong
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That strategy ends in deep regret, because it requires you to opt-in specific bits of data. If you ever actually need it, you will discover that something important was missed.
(Also, if backing up data is at all painful, it means you are doing it wrong.)
It depends how you do it. Some of my data is backed up via Google drive in almost as automatic a way as is possible. Add a new folder to your documents library (Windows 7+), make this folder the default save location for the library, make it the folder where google drive manages backups automatically (there is a program you download to do this). Now you just need to pick the documents folder whenever you initially save something important, and the rest is handled for you. The same would be easily doable with dropbox.
That strategy ends in deep regret, because it requires you to opt-in specific bits of data. If you ever actually need it, you will discover that something important was missed.