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When I use outline stroke, it's creating points in a very strange way. In my image where I marked 1 and 2, you can see that it doesn't make sense why it would be placing the points in that order. I'm having a little trouble describing the issue but hopefully someone can get the idea from the images. In the last image I used the smooth line tool and you can see outline stroke is placing the points weird. It's never done this before.
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What is that? A calligraphy brush?
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I think it is, it's one of the default brushes, 5 pt. round. It doesn't do it with basic stroke, but it's also never done this before with that brush
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Then just assign a plain stroke instead of that brush before outlining.
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I suppose I'll have to start doing that. It's just strange because those brushes have never done that before when outlining. I also figured out that pathfinder merge fixes the issue for the most part.