endmill holder trouble

No worries. I was looking at it and thought it would be an awful small counter bore to improve accuracy.
 
Yes. But I can see it wobble when turning it in the mill by hand.


In that case, it may be that the hand reaming operation is causing a tapered hole. Is it possible to ream in the lathe after boring? Or to bore to size in the mill?
 
I have the start of another one in the lathe now. I'm going to get the threading done first then work on the 3/8" through hole. I purchased a reamer to go in my tailstock and will be doing this all while still chucked in the lathe. Hopefully this one will turn out well.
 
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