Here's a series of examples for various options (random character chosen, this is a font A, not someone's specific logo):
In other words, a setting that measures the dimensions of the entire shape, stroke included, is what I am looking for. The width of both object, stroke (separately, for production reasons), and overall object (again, for production reasons), are important. (I'm only really including the third option as a permutation of the settings; it's come in handy for original art but I'm not suggesting it's a fix).
In the instance of actually getting someone's vectors, this is extra important-- the pre-existing form of the logo will probably have aligned-to-center stroke lines and that won't be something that you can just decide not to follow.
Caveat about the enamel pin example: of course those cutouts are a bit ridiculous, but since I wanted an example addressing how outlines are achieved, I'm not bothering with that, it's just not relevant.