Here is the tale of two individuals that upgraded to WordPress 3.1 only to realize that their sites became broken after the upgrade. Two things that should immediately be learned by anybody using WordPress. The first is that even though it’s as easy as clicking a button to perform an upgrade, that doesn’t mean you shouldn’t create a backup of the site before the button is pressed. The second point is illustrated by Keith in his story:
The recent 3.1 update changed my thoughts about that and taught me that even a hobby WordPress blog isn’t entirely automated and it is a good idea to know how it works, if you care about it. If you are passionate about your blog, there is even more reason to anticipate disasters and know how you react to them accordingly.
If you’re going to pour your heart and soul in to your site and it’s running WordPress, you would do yourself a lot of good to learn the basic ins and outs of the platform to not only help yourself, but to understand some of the underpinnings that allow WordPress to do what it does.
The one other piece of advice I can provide is to wait a few days after a major version of WordPress has been released. Keep an eye on the WordPress hashtag on twitter and the How-To and Troubleshooting section of the WordPress.org support forums to locate the issues people are having once they make that upgrade so that if you run into the same issue, you’ll know how to deal with it.
As an aside, my streak of problem free upgrades continues as I had zero issues with 3.1.