jleslie wrote:
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I tried that (Make Hole) with my odd-shape polygon, but the vertex's kept overlapping and being hidden...
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That's due to the odd shape of the polygon, and the desire to end up with a round "hole". I imagine you'd need to either set the Make Hole % low, so that the vertices are created and grouped closer to the center of the object, and/or remove (or Snap/Weld!) some of the vertices to get a smaller number of vertices remaining on the interior hole.
I hear (and commiserate with) your frustration at the need to sometimes draw surfaces "by hand" (e.g., select three or four vertices counterclockwise, and Ctrl+Shift+S) but sometimes that's the best and cleanest way to get what you want. Booleans just won't do it properly, and you'll spend more time cleaning up Boolean mess than you will with other methods.