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I have 2 sites active, WordPress, and there are five or six updates to things running on the site. I read the faq here, “Updates: Stay up to date with all plugins and core software at all times if you don’t want to have security holes and get hacked.”, but scared of blowup.. I guess I should take one at a time and see?
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If you are using popular, well known, well supported themes and plugins, you should not have any problems. Problems arise when you use plugins that only have a small number of users or those which don’t receive updates for long periods.
If you haven’t run an update for > 6 months, you might have issues, so it’s best to test on a staging site.