Thinking about it after reading this thread I may have been my own bad luck setter depending on how the algorithm really works.
I had assumed what it would do is more of a lottery so a person would be picked at random and than it would go down the list of their software picks to give them their "most happy pick" based on what software was left. Now that I really think about what "Maximized" happiness really means I realize my odds of winning anything were extremely low since I only had one thing at 100% as I had carefully scaled only a single item for each % chance.

I now think that the way it probably worked is that it lumped the highest happiness together and than pulled a random person out of each of the highest pools. So given that there was likely many people with 100% for every single item really that means I probably only had once chance of actually winning something and than simply ignored for all the rest of the drawings. XP

Any progress on this?