In our experience, the majority of WordPress site owners don't regularly back up or update their site because there is significant pain in doing so. Updates often break things on the site, and backing up can be hard.
We created a WordPress backup, update, and monitoring service to solve this problem. We back up your WordPress site daily, weekly, and monthly, and store your backups on a secure, offsite server. We update your site as soon as updates are released, verify that the updates didn't break anything, fix the issue if something breaks, and monitor your site for malicious activity. Let us know if you'd like us to set it up on your site. http://ow.ly/iRSAc