In my previous post I rambled about a bug in the Web Application .targets file. I found an easier solution which does not involve patching any existing files.
The solution is to add the dependency projects to the msbuild target list like so:
msbuild /t:ResolveAssemblyReferences;_CopyWebApplication
/p:OutDir=..\Drop\bin\ /p:WebProjectOutputDir=..\Drop\
Wow. Life CAN be easy.
Update: Even more so, it is better to use ResolveReferences, which also copies any project assembly references you have in your project.
Update 2: You actually need to add a 'bin' directory to the OutDir folder.
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