On another blog, I saw a feature request to be able to script start debugging so that the debugger could launch/attach to multiple projects. There isn't automation support for launch, but there is something that is easier to use - a solution can be configured to launch or attach to multiple projects. To do this, open solution properties, and under the 'Startup project' change it to 'Multiple Startup Projects'. Combined with exe projects, and exe attach projects, this gives you a fair amount of flexibility in customizing F5.