If you can't recoup your costs after a couple of decades your work either isn't worth anything commercially and/or you are incompetent in business. Regardless of which, society would probably be better served if you were out of the way and the work could be leverage by others.
When copyright expires the work becomes public domain, it doesn’t get a permissive license with restrictions (MIT). Also, expired copyright doesn’t mean you get access to the sources from the creator; when Mickey Mouse becomes public domain you don’t get access to all the original animation cells and drawings, it just means you can draw the character yourself and use its name however you please. Finally, decades-old software doesn’t have the same cultural importance, only a tiny amount of people care.