I've shot a few deer with stone points over the years. I've honestly never noticed a difference on an animal between a properly sharpened stone point and a properly sharpened steel point....which shouldn't be surprising since the stone points fed people for tens of thousands of years before we invented metal. My one caution would be that people make a real effort to learn how to PROPERLY sharpen a stone point. I have been playing with flintknapping since the late 80s and I still need to concentrate and make sure my technique is good when I am putting a hunting edge on a point; remember, it won't feel like a steel edge because it works a little differently, but its just as deadly. I also would caution folks on obsidian....yes, it is absolutely easier to make a decent point and it is easy to sharpen, but that also means it is easy to break. Get some good chert and you'll be happier and the heads will be tougher for sure.
I slot a wood shaft perpendicular to the grain in the same way you would for a self nock. I always encourage people to use real sinew rather than the artificial sinew. Artificial sinew will certainly work, but it is made from nylon and it stretches significantly. Real sinew, applied wet and then allowed to dry will shrink and bind the head TIGHT. Also, make sure you have a smooth transition to the shaft and also don't skimp on the sinew. I see a lot of heads that don't have sufficient sinew to prevent the shaft from splitting if you hit something hard. Also, remember that if a stone head breaks inside the animal, it will by definition reveal a new razor sharp edge and will continue cutting.
The point on the left has passed through two deer and is ready for a third.