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I can reproduce the issue, so you aren't imagining it. After a bit of testing I noticed it only seems to affect objects with Bézier curves. I tried it on rectangles and the Intersection boolean operation works perfectly, so I suspect the inaccuracy is due to fact that Bézier curves are not capable of creating mathematically perfect circles, at least not ...


The blue shape is subtracted from the brown one in three cases. In the left the result is a group of 2 separate paths. In the middle the result is a single path. In the right the result is a compound path. It's the way how Illustrator presents paths which have holes. Not asked: A path can be drawn with self cutting edge. It also can seem to have a hole, but ...


If the Minus Front operation results in a single closed path, it just returns a single path. If it results in several unconnected paths, it returns a group. If it results in a shape with a hole in it, it return a compound path. If you hold down Alt while clicking the Minus Front button, you get a compound shape where the bottom path is "positive" ...


As @joojaa mentions in the comment.... Remove the new stoke and choose Object > Path > Offset and enter a value half the size of the stroke you removed.

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