Okay, so here's my new thought process: I've got 10 stories I've been planning to publish in a single volume. I've decided to used the $0.99 cent price point, mainly because I know how well it works for people in the Apple App Store. Sure, I won't make all that much money, but that was never my goal in the first place. (Okay, deep down inside I hope that everyone in the world buys my books and I can retire to a tropical island, lol.)
Anyway, of my 10 favorite stories, there are 9 that I really REALLY love. So I've decided to publish 3 books, each with 3 stories, and simply omit the 10th story. This fits in great with my idea of using my girlfriend's painting on the covers, because I've taken several different snapshots of the painting and can easily create 3 cohesive covers for the books from the photos. This will also give me a chance to publish the first one and see how it looks, then modify the 2nd and 3rd book accordingly.