There are 2²⁵⁶ public/private key pairs. There are 2¹⁶⁰ bitcoin addresses. So, for each bitcoin address, there are 2⁹⁶ public/private key pairs that produce it.

To find the private key for a particular bitcoin address, you may still have to search up to 2²⁵⁶-2⁹⁶+1 private keys because you don't know which ones give duplicate addresses. However, assuming everything is randomly distributed, the probability of any private key generating a particular address is still 1/2¹⁶⁰.

I make the distinction, because it is possible that you could try all private keys from 1 to 2¹⁶⁰ and still not find a match. It is possible for all of the 2⁹⁶ keys for that address to lie somewhere in the range from 2¹⁶⁰ to 2²⁵⁶-1.

#1 is not necessarily correct.
#2 is correct.

Also, remember that 2²⁵⁶ >> 2¹⁶⁰ >> 2⁹⁶