One can install https://chrome.google.com/webstore/detail/high-contrast/djcfdncoelnlbldjfhinnjlhdjlikmph today, flip pages to high(er) contrast and the change applies when printing too, at least when I tried with a simple page of text without any CSS print media. My initial questions are:

1. Is it worth it to build it in to Chrome, vs building it as an extension.
2. How to do the automatic part.

This issue has been Available for over a year. If it's no longer important or seems unlikely to be fixed, please consider closing it out. If it is important, please re-triage the issue.

Sorry for the inconvenience if the bug really should have been left as Available.

For more details visit https://www.chromium.org/issue-tracking/autotriage - Your friendly Sheriffbot

+lpalmaro for an opinion.

I think this is a good idea. Leaving this open as an Available feature request.