There is a software company, called Softsearch. that sells applicant software for online job applicants for school districts....they they have gone out of their way to make it complicated and difficult at best and looks to me it was made with Windows in mind...nothing is intuitive and everything DEMANDS answers even if the question has no relevance to the job you are apply for...looked up the help line and they only have voice mail and do not return calls. This is prime example of the arrogance of people who write software and impose it on people just trying to get a job...hundreds of thousands of teachers in years past were hired with a résumé and reference letters...but now....they have made it complicated at best. the concept of K.I.S.S. has been totally lost in the Geek community..
First, I completely feel for you. Second, go somewhere else. I'm a software developer ( MacOS, iOS, Web Application - Front/Back End ) and write applications like this everyday. There are many others that do the same.
KISS is very strong ( often the most important ) in the interface design of most software today. Having typed that, there are many 'old school' that had the software written 10 years ago and are still selling it today.
I'm sorry for you and everyone that uses that software. There are other solutions.
PS. We are a bit arrogant, but the best of us use comments like yours to double our efforts to produce quality, user friendly software. I'm currently working on someone else's project that has similar issues: Such as the inability to sign out, once signed in. And I mean forever, signed in. Searching thousands of lines of spaghetti code to find the single if-then that writes out a combination of session, local storage AND cookie credentials is difficult at best.