Work wise, I have decided to move past auto deploys, probably forever, and upgrading our Ruby version, for now, to focus on other more feasible tasks. One such task is optimizing our load times, specifically optimizing images. I noticed we were serving up some pretty unnecessarily large and uncompressed image files, multiple megabytes in fact. Subsequently, I ran all the images through this awesome, free compressor: http://optimizilla.com, and was able to cut the image payload in half.
To test this optimization I uploaded the compressed images to just our staging server. The result: our staging server, a Raspberry Pi 2 run out of my apartment (http://imgur.com/a/khE8L), was just as fast or even slightly faster than our DigitalOcean VPS. Incredible. 😲
Lastly, I added CloudFlare to my personal site. Full HTTPS for no reason, woo! 😄