I think automatic updates are a great feature in Visual Studio 2010. Each time an instance of VS 2010 is opened, it automatically checks for updates to installed extensions.  When updates are found it then kicks off a quick and painless process to install new updates, and all from within the VS 2010 IDE itself.  There’s no need for you to check manually to see if you’re up to date on an extension, you’ll see a VS 2010 notification icon in the tray area which give us the following options:

If you choose View Updates in Extension Manager you’ll be taken to the Extension Manager dialog window where you can choose to update your extension(s).  In this case, I have the VS 2010 Pro Power Tools ready to update.  On the left, you’ll notice the number of extensions that need updating, as well as links to installed extensions and the online gallery.

Once you choose to update, you’ll need to restart VS 2010, but you don’t need to remember to do it manually, it will automatically ask that you restart.

Now THAT’S an easy way to get updates right in VS 2010 with full control and without any hassles.  Extensions install quickly and painlessly.  If you’d like to change the auto-update settings at any time you can choose the Tools->Options menu or alternatively you can choose Settings from the context menu on the try notification icon.  You’ll see the Options dialog box with the following settings:

You’ll want to keep the “Automatically check for updates to installed extensions” selected to take advantage of this feature.  This little gem ranks high on the usability scale, as it’s stress free to find then keep extensions up to date.l