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I was a CAD manager for various multi-disciplinary engineering firms in my early career, I can attest to some of the accounts regarding various CAD systems already mentioned.

One not mentioned that comes to mind is E-tap, used by electrical engineers. Well into the five figure territory once all the various bells and whistles were added.

However the most expensive software I ever saw in the wild was some little known simulation platform for a mathematician running predictive models (it also did this with 3D graphics, so both senses of the term) on mine/rail/port operational scenarios. That was into low six figures a seat and five in annual maintenance.