Well, for one thing, the image that works has a lot more dark text on it, whereas the one that doesn't not only has less text, but some of the text that it has is greyed out.
At the end of the day Tesseract is going to be working on a bitonal image, since you've got a non-traditional application, I'd think you'd want to control as much of the image preprocessing as possible to make sure it's getting done in a way that's appropriate for your application, so rather than converting to greyscale, you should threshold and convert all the way down to bitonal.
Tom