Folks,
I found training portion of tesseract quite challenging. In order to simplify it I have created an application to get bounding boxes for an arbitrary text and fonts.

In essence it is IOS FontTrainer application that runs in XCode with IPad simulator.

Font trainer allows font selection, new fonts could be downloaded and added as well. Setting screen allows to selected desired fonts and font sizes, drag and drop a training text and initiate a measurement flow. The tool generates bunch of artifacts - with extensions - txt, tif, box, font_properties.
I use the tool to create a training set and found it useful. I wonder would it be useful for others ? In case if it is something other folks want to explore I will publish it.
Thanks