Currently, I'm converting all the jpegs to webp at 55 compression at the time of import and I love both the quality and the sizes of the files, and so far couldn't be happier with the results[0] I managed to shave some 20GB from the disk usage as well.
The 800lb gorilla is, however, Safari. We all know that Safari does not currently support webp and due to internal politics, may never do so.
So the first "solution" is to keep copies of both formats and use the <picture> tag. This just won't do I have zero interest in doubling my already prodigal disk usage.
There are some rather complicated OS libs that will take a jpg and convert on the fly to webp...I want to do it the other way around.
One thing I hate are "kitchen sink" libs that do SO much that you are often left confused on how to do the specific thing you want to do, so I am in the process of rolling my own solution by using GD and intelligently converting the 11% of all requests that are Safari and using nginx caching to keep these converted images ready to go.
I would like to hear of anyone with better solutions, if possable, since as you can see, I haven't yet implemented my ideas.