100 shares at $100
100 shares at $50
This will satisfy your demand curve.
In a direct listing, the initially listed shares will all transact at the same price (the clearing price).
Are you saying that an auction of this kind is a bit complicated, and it's possible to make a mistake? I suppose that might be true, but that is a very different assertion from your original position:
"since people had to enter a single point on their demand curve as a price and quantity of shares (instead of their entire demand curve)"
100 shares at $100
200 shares at $60
This will satisfy your demand position.
I would still enter two bids; it's just a matter of adjusting how many at each level.
All the shares in the auction are sold at the same price. If the market clears at 60, a person entering the bids I described would buy 300 shares at 60.