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I’m late to the party, but using a 3/8 round over bit will probably take off no more than 1/8 inch at the deepest part of the cut. I see no reason to not remove the material in one pass on most woods that behave well. I do it frequently with no issue.

I just needed to do 3/8 round-over on hickory for 1/4 round trim. The Hickory did not behave well so I had to reverse cut it, but I was still able to do it in one pass.
 
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