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I like Bauer's idea.

You can just start at the outside with the router and work your way to the center. However, as you get deeper, you have trouble with getting the router close to the outside. You'd essentially have a little ledge every time you reached the maximum bit depth.

But that's the inside of the planter, so maybe not so bad?

Or maybe a ship auger bit? Or a six inch regular bit? On a circle jig?
 
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