MjG0001 wrote:Completely new, lost, and overwhelmed.
New to Pi, or new to programming?
At what point did you get lost? You have a fair definition of what you want, enough to get started
What part has overwhelmed you? The usual answer is to divide the problem and solve it bit by bit. So:
Get into a programming environment (C++ or Python -- I'll come back to that).
Write a "Hello, World" program, get that working.
Find a GPIO library, import it and get an LED flashing.
Arrange to read the GPIO that tells you whether the device worked.
Complete the integration of the test hardware, with a convenient way of connecting the "Device Under Test".
Put that lot together to do a one-off Pass/Fail test.
Put that in a loop, control the delays and number of attempts, count the results and display them.
Rewrite it all , making it better in the light of what you have learnt.
Assess your ideas for improvements, implement those that are worthwhile.
Job done, though possibly never finished (see last step above

)
Why C++? A respectable language, great if you already know it.
But Python is probably better supported on the Pi, and has a more interactive environment. It's interpreted rather than compiled, which makes for a quicker build/test/fix cycle.
If you don't know either, Python is a less steep learning curve. There are good learning resources online, for example
Code Academy. There is an extensive GUI library (TKinter).