See, that's not how I remember the 90's. I remember getting offered floppy disks with every bit of software out there. Their overly restrictive copy protection often consisted of "what's the 5th word on the 10th page of the manual" or similar.
The prices were not really outlandish, though they were representative of catering to a new and niche market. It's just that the barrier to copying was so low and distribution was so easy and risk free.
Basically, it was the equivalent of a physical store with no employees, locks, or security systems. Thus everyone went in and got what they wanted without putting money in the "honor box".
I was thinking more about movies and music. I would agree with you on software, more or less, but I think adding DRM was inevitable once the capitalists got control away from the engineers and inventors.
After all, why sell what you can rent?