I run two instances of visual studio--one for the external dll and one for the main application.
In the project properties of the external dll, set the following:
Build Events:
copy /y "$(TargetDir)$(TargetName).dll" "C:\<path-to-main> \bin\$(ConfigurationName)\$(TargetName).dll"
copy /y "$(TargetDir)$(TargetName).pdb" "C:\<path-to-main> \bin\$(ConfigurationName)\$(TargetName).pdb"
Debug:
Start external program: C:\<path-to-main>\bin\debug\<AppName>.exe
Working Directory C:\<path-to-main>\bin\debug
This way, whenever I build the external dll, it gets updated in the main application's directory. If I hit debug from the external dll's project--the main application runs, but the debugger only hits breakpoints in the external dll. If I hit debug from the main project, the main application runs with the most recently built external dll, but now the debugger only hits breakpoints in the main project.
I realize one debugger will do the job for both, but I find it easier to keep the two straight this way.