The tapers on those keys are often needing adjustment to fit properly to the crank and flywheel. Sometimes they lack the taper altogether. With a proper taper, they will go all the way into the slot to within about 3/8 to 1/2 inch of the flywheel and be fully tightened. I know it is much better to see them this way (easily removed and adjusted), than driven in too far with a 20lb sledge!
I have seen that problem and it can present a real challenge to remove without damage.
A good dressing with a sharp file will fix the issue in most cases. I also like to use a little bench belt sander around the shop for minor adjustments as well.
Butch, you most likely have some good rule-of-thumb wisdom on the topic... bottom line, don't trust the Indian finished parts to be perfect right out of the box.
dieselgman