I would recommend against a tapered end pin and go with a screw type like this one.
http://www.stewmac.com/shop/Hardware...t=3&xsr=251725
For that type, just drill a hole slightly larger than the size of the solid shaft of the screw (outside diameter minus threads). I like to put a bit of wax or soap on and then screw it in.
Are you putting one on the heel too? That can be a little trickier. I think Frets.com has a whole page devoted to strap pins.
Good luck.