Should I decouple useful code from boilerplate?

[OmegaSEX]

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[fschmidt]

There is something missing in this story.  If you "need to write about 100 lines of additional tedious-to-write code into these source files in order to link it" then how would linking to a shared object library work without such code?  And if there is some way to automate linking then you should be able to automate using C++ files in another directory.  Without fully understanding this, I agree with your boss.  Best to have one executable and figure out how to organize the code to remove the pain.