The issue was due to the variance of image size. An image that is significantly larger than the page average will be loaded slower since all images get an equal share of bandwidth (priority).
We could further improve first paint times by pushing render blocking resources but we'd need to be serving those resources off the 99designs domain (with current push implementations). This opens us up to a class security issues we avoid by having an asset domain i.e. types of reflected XSS and serving cookies on assets.
For now we'll wait for the webperf working group to address the limitations with server push semantics.