In Visual Studio (2008) is there a way to have a custom dependent file on another custom file?

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There is VSCommands add-in which allow you to configure dependant files directly from IDE

Link updated, previous was http://mokosh.co.uk/vscommands

FYI: When VSCommands is installed, just select all the files you want to be Dependant and the root file, then Right Click -> Group Items… and VSCommands will ask which of the files you would like to be the root file.

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