POTD- PROJECT OF THE DAY: What Did You Make In Your Shop Today?

You should not have to rough out the slot. Shorten it as you describe. I would check your rake angle. I would suggest trying to get about 5 deg of rake on the end. If you left a 90 deg corner there then you actually have a negative rake angle and will get deflection. What angle do you have?

Edit: I just checked my tool. I have about 5 deg or relief and a minimal positive rake angle, maybe 2 deg. Keep in mind that rake angle is with respect to the direction of motion, not the axis of the cutter which in your case is angled.
Actually sharpened the tool and it worked quite a lot better. Well enough to let me take about 0.004" cuts and generate some curly chips.
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Finished slot in new pulley

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Now I just have to locate the center of the keyway vertically and drill & tap for the set screw. Some tables I looked at on the web call for 1/4-20 set screw for a 5/8" bore and 3/16" key. That seems big to me - should I go with it?
 
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I'd agree on the 1/4 key.
I'd also drill, tap and install a square head pointed lock bolt 90* of the key way. Yup, straight from the 1920's, but at least the thing won't fall off the shaft.

The man a couple posts down is right about not running 180* on the second screw. Post adjusted accordingly
 
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I'd agree on the 1/4 key.
I'd also drill, tap and install a square head pointed lock bolt opposite of the key way. Yup, straight from the 1920's, but at least the thing won't fall off the shaft.
I am going to install a second set screw 45deg from the first. I can't use a bolt as you describe as I am drilling in the bottom of the Vee and it would foul the V belt. The motor shaft is barely long enough to support the two sheave pulley and no room for a longer hub on either end.
 
I am going to install a second set screw 45deg from the first. I can't use a bolt as you describe as I am drilling in the bottom of the Vee and it would foul the V belt. The motor shaft is barely long enough to support the two sheave pulley and no room for a longer hub on either end.
Good choice. Two set screws 180° apart create a pivot and would be about my last choice.
 
I am going to install a second set screw 45deg from the first. I can't use a bolt as you describe as I am drilling in the bottom of the Vee and it would foul the V belt. The motor shaft is barely long enough to support the two sheave pulley and no room for a longer hub on either end.
your V belt should not be riding in the bottom of the V. It should be further out running on the sides of the V.
 
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