That being said, Paul, making the testing connector a connector board itself that plugs into a mother unit can be fruitful, as it's easily replaced. If the testing requirements are numerous enough, it could be worth it.
However, we solved our similar issue by making up a pair of connectors that looped signals back and forth, with only two test points, one at each end of the string. After a set number of uses, these pairs were replaced.
Obviously, these would be made up for every unique cable set to be tested, but it at least allowed a simple go-no-go test for every cable set. Also, one can sometimes find high-cycle-count variations of the connectors of interest, allowing a tester to have better quality connectors than the cables being tested.
C
The types of cables being used in this case have hundreds if not thousands of connect/disconnect cycles. I'm not concerned about the physical aspect of the project, but more interested what avenue to go down in the software aspect (albeit, the hardware used in the testing circuit is also part of the question).
Well, software wise, there are only two paths. The first is to supply a table of what tests should be made and the expected results. The second way is to write software so the program can create a similar table of what a good cable looks like.
I don't think an Arduino is suitable for either.