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Eclipse has a great option for the debug “Watch” window called “Show Logical Structure” which makes Collection objects way easier to inspect. Instead of showing the gory member fields of an Collection instance (like a hashtable, for instance) it instead shows an easy-to-read ‘Cliff Notes’ version.
Does a similar option exist for Visual Studio?
Have you had a look at VS Visualizers
for ASP.NET 2.0 Development
Debugger Visualizer for VS.NET
Debugging