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I go right to 1/2" roundover all the time right to the finish depth with no problem.
If I suspect the type of wood may splinter or something, I don't do the first pass flush(hold it up a bit) then do a cleanup pass. You can also run it backwards a bit doing a climbcut, but for roughing out plugs that is getting a bit overkill.
if you are doing short pieces, then use a router table with a fence and a pushstick, that's the safest way
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