It turns out one of the better features added to Visual Studio 2005 is remote debugging. It is actually quite simple to set up. The only caveat is that you have to be an administrator on the remote computer. It works by using a Windows Service that runs on the remote server. To install this service on the remote computer, simply run rdbgsetup.exe in the vs\Remote Debugger\x86 folder of the Visual Studio Installation DVD.
That will install a service as well as install an application that iwll let you monitor incoming debugging sessions. If you have windows firewall enabled on either computer, you will have to allow some ports to be open. You can find this information in the Visual Studio Help.
To start remote debugging, make sure that the web site that you have deployed is in debug mode. If it is precompiled, choose the debug option, so that the pdb files are emitted when compiled. Then, open up the solution in Visual Studio on the client machine. Go to the Debug menu -> Attach to Process. Type in the remote computer name and then you will see a list of processes. Click on the w3wp.exe process to debug the ASP.NET application, set some break points, and then hit the application in your web browser.
Also, I discovered that you must have the Remote Debugging Monitor open on the remote machine for you to be able to attach to the process.
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