I would first drill in with a 1/8' bit & finnish with a 1/4" or a little bigger if you have one. We finnished & tapped in 1/4" & to date they are still holding. One I did six yrs. ago. Go luck. 
Ok Thanks i Appreciate your Experience and the tips. I thought you ment drill from the top thru the gear teeth then pin it that way.
Your way makes 100% more sence its a great trick!
As far as the Machinists key it will work as they Machined out a big Oval shape in the crank (look at my Picture)
Its a almost perfect long slot with rounded endes all the exact depth.
(the shop that did that cut with a milling machine had the cRank outa the engine)
Anyway there was traces of the ORIGNAL woodruff key slot in the bottom of that Oval cut out.
Its Dead center in the Oval. So the Machineist is makeing up a new piece to fit in that oval with the key part sticking up..
Basicly makeing the crank like it was when new but a werid shaped key.
But as added Strength i like your idea of drilling a 1/4 inch hole beside or down the joint of the pully and Crank.
I will take some more pics and post em here now the Crank is clean and that Worn hand made piece of crap key is gone, Once my buddy has made up the new Key way.
New pulley will be here tomorrow from GM.
Should be a good Repair.
I have a new Longer crank bolt two the orignal one was way to short!