This was my first time using 99 designs, but not my last!
For me I looked at how well a designer could not only design the image, I also looked at how well the image and the font matched (some designers had round images and sharp font). In addition I looked at how well the lettering balanced with the image. Based on that I took the best six designers that had their own take on the image, no two images were the same and all six could have been used as my logo (all of my final six were very high quality designers). In the end it came down to an image and lettering that could be viewed as many types of hats with lettering and colors that matched the feel of the company.
Sorry I could not responded to each and every message that was written to me, there were just too many and I was trying to give feedback on the designs.