Nah, list them all at the same time, .99 cents each, and offer combined shipping. One lot might simplify shipping, but you have to count on getting a few of the BIG TIME clock freaks excited. With all of them separate but listed at the same time you should get lots of collectors buying multiple ones to combine shipping, and bidding against each other, etc.
I have noticed it in the past selling NES games. If I list 1 game I am lucky to get the $1.50 asking price. If I list 100 (separately) at once they will average out to like $5 each.