Hm~, I’m not sure software is to blame, rather than just problems with timetables in general. I tried finding something more concrete, like descriptions how trains dealt with this historically, but I only found that this is apparently the most common way to solve the problem all around the world nowadays, and no useful historical documents (search is so broken x<).
And now I discovered the closest rail library to me is a major city over (so not in the closest one), and their online catalogue only returns one maybe relevant result, in French, and it’s not on scihub.