Virtuoso is the VLSI layout editor/schematic toolset that is egregiously expensive. However, I believe that Allegro (the PCB suite) is above $100K per person per year.

A good example at the price range cited is ballroom dance competition software. Dick Douglas created it a number of years ago and people gripe what it costs (I think $1000 per comp or so) and the fact that it hasn't been actively developed over the years. It would be very useful as open source software--except that nobody seems to have the knowledge of what is needed (Dick and his wife Liz have high domain knowledge of ballroom scoring and competitions) and nobody is willing to take on the training/customer support task.

This is, in my opinion, where software, in general, breaks down. Everybody wants to be the developer of scalable software that doesn't scale support costs--unfortunately, that's the exception, not the rule.

(Link to the ballroom software: https://www.douglassassociates.com/)