Is it already possible or can it be made possible to simply rewrite original images with optimized versions instead of reinventing the wheel every time the cache is cleared or they are evicted for space/expired?
Possibly not as a default, if there is any danger to it, but as a setting? People can backup their images in case of disaster and let pagespeed rewrite them as needed. Any image that dies badly can be restored from backup and put on some forbid list.
Will likely free resources for the more dynamic work pagespeed has to do and give more speed for same result.
Or possibly some setting for resources that will never change and those that will - css/js files with version numbers and images for example. Why cache? Just replace with the better version (where permissions allow, of course).