I'm also not sure if the automation actually scratches any real itch - I doubt that people try to run 'less' on CD images or 'ar' archives when knowingly working with files of that sort.
This is a trend not uncommon in GNU software -- features added by someone who at some point thought it was a good idea, but probably didn't even bother using them much beyond an initial test to see that they are somewhat working. Most users likely think of 'less' as nothing more than a bidirectional version of 'more', and not as the "file viewer that attempts to do everything" that it seems to actually be. It's also a little reminiscent of ShellShock.