You're assuming their technical illiteracy is limited to software. My mother routinely must explain to teachers over and over that files saved to "their desktop" are accessible from any computer on the AD, or that Google Drive is different from email.

I'm well aware that there are plenty of teachers who flat out suck at technology, software, hardware, or any layer in between. But it's not binary, more of a spectrum.

I'm just offering up a possible reason that someone wouldn't want to learn. I strongly believe that most of the current "hate on learning new computer systems" is due to programmers and designers more than cranky users