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3

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 ...


3

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 ...


2

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" ...


1

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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