I think you're just recalling the few software products that were actually good. There was plenty of crap software that would crash and lose your work in the old days.

I always found it funny how Word on Window 3.1/95 would have a day dream moment and just completely lock up, usually when you were about to save the document

I still save stuff every few minutes out of habits formed in the 90s.

Old DOS stuff could either be a total nightmare or some of the most brilliant code you had ever seen. Thats just the way having no giard rails goes.