What I am seeing is that:
1. Bob always checks the standard forms and there were no other responses from certifiers.
2. Justin provided an example of how a home made computer program can:
a. lack intuitiveness as evidenced by my question
b. has the potential for unforced errors as evidenced by Mark's question
c. is going to be tricky to use universally as evidenced by how confused I was after reading about how to (safely) install and use DOSBOX.
The system could very easily be converted to a standard Excel spreadsheet (or Open Office if there is a commercial use issue). This would allow (force the "thinking through of) standardizing such things as digits of precision required at every step or what was done to adjust course distance to the desired distance.
I love the State of Franklin Track Club's "automagical" Event Calendar because it forces race directors to think through things they commonly ignore. It (largely) saves me as a timer from unnecessary awards errors.
Once you have forms converted to a tightly macro'd spreadsheet, the only thing transferring to the pdf's can do is cause the poor certifier more nuisance errors to straighten out with a careless or poorly informed measurer. Maybe it would even force the measuring community to once and for all to resolve / standardize the "sum of the shortest segments" issue. I still have a bee in my bonnet for having been sent back to the first course I ever measured commercially for something that is not in the manual.
Justin, if you have that DOS source code in something like C or Basic, I will be happy to rewrite it in directly executable Windows code. However, I think the conversion to a thoroughly "thought through" spreadsheet would significantly simplify the certifier's task.