Trying to work outside the perimeters of the OS is not a valid complaint of it being broken.
Absolutly.
.info files do exist in Windows. They are shortcut (.lnk) files.
In the 80's, people were figuring things out, and had to work with limited resources. Today, there is really no reason not to take the best of all worlds. Today, an OS should first check for a .info/.lnk file to see if there is a file specific configuration, and if it doesn't find one, it should check the inside the file for a filetype to decide what to use to open it, and failing that, should drop down to using the file extension.
While that would have been a huge burden to the hardware of the 80's, in today's hardware, it would be trivial.