Autoload is fundamentally broken because it makes your app state nondeterministic by making state loading and logic interdependent.
I work on a large Ruby software project and we've had to move away from any autoload except for very specific cases for this reason- troubleshooting autoload bugs are the WORST.
Maybe this is the reason it hasn't been looked at.
I wish. There was a window of time when Matz said autoload would be deprecated. But he took that back after Yahuda (I think) addressed some threading issue. I agree with your assessment, but too many big names project use it --RubyGems, Psych, Rails, etc.
I wrote my one load system but have never been able to use it 100% with other projects b/c I could not override autoload require. Though I've begged for years Matz just keeps blowing it off.
I work on a large Ruby software project and we've had to move away from any autoload except for very specific cases for this reason- troubleshooting autoload bugs are the WORST.
Maybe this is the reason it hasn't been looked at.