There are a great set of troubleshooting labs for .NET, seven in all, over at Tess' blog. It deals with different troubleshooting scenarios and provides step by step instructions for dealing with each of them. They do not take very long to set up and go through, and it really helps identify some of the core debugging issues.
Tess is a Microsoft employee who has been blogging about .NET debugging for years and she really has a great talent for troubleshooting.
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