Unfortunately, you can blame malware and long wizards for making users afraid of updates. I know lots of regular users that just wait for their local techie neighbor every 6 months or so to patch up their system.
The only real solution IMO is for software developers to start using update systems like what Google Chrome uses: Transparent, automatic, and don't ask the users any questions. Just install the update.
Whenever I set up a system for a user that isn't tech savvy, I always make sure Windows is set to update automatically, and if I'm allowed to, I install the newest Secunia PSI, which has the ability to install many application updates automatically.
Sadly, not all applications have the ability to have silent, automatic updates, but whenever possible I enable them.
It's less work for myself and my users if updates are automatic. And to be honest, it's how things are going to work in the future.
While it's certainly good to allow some users to set updates to manual if there are compatibility issues - I think that by default, they should be automatic on all software, and I think that all non-web software should embrace the update model that Google Chrome uses.
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