Yea, I read through the LoadFromFile configuration stuff and it turns out that should only be used for static files. In my case images are being dynamically generated into the proper size from the master image. So, doing LoadFromFile isn't recommended and/or feasible due to that. And since the cache headers are a month and the recommendation is to up that (as we both know one month should be plenty to avoid this) I doubt increasing it more will help.
Also after this update I seem to now not be getting webp images out. So, I am going to do some tweaking to the config of both pagespeed and the backend tonight. Then I'll chill for a bit to collect data and see if things improve and report back at some point next week with more information.
I have updated to the latest release about 3 hours ago. I am now with 8.43% cache misses, 3.61% on cache lookups expiring, and for the first time 2.35% failing from the domain not being authorized. This last one (authorization of domain) could be something I just did messing around, so I wouldn't put much weight in that one until I reconfigure things in detail tonight.