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TortoiseSVN does have an analogue to 'svn status -u'. It's the menu option labeled "Check for Updates". I didn't realize it was there for the longest time and actually lamented the lack of functionality.
I'm not sure when it was added. I'm running TortoiseSVN 1.1.1.
For my use, I love TortoiseSVN. It's friendly enough that my boss (not really a command line guy) loves it, and it's got enough added usefulness over the command line client that it's usually my first tool for hitting the repository here. (I still use the cli client for scripting and such.) One of the features that I really like is the integration with a bug tracking system, so I can jump directly to bug listings from subversion changelogs.
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