Toasty,
That's a great initiative and the tool looks promising.
Coincidentally, we've been working on an article based on
https://nullsweep.com/http-security-headers-a-complete-guide/ to help with headers settings. But obviously, your solution is better that a simple article.
Regarding, the lapsed license, please get in touch with us in case you need renewing it.
Regarding the score, it would be better to be more tolerant with some use cases: for example sites which have no iframes for example and which (knowingly) do not include headers related to frames and their origin.
The above suggestion may require some deep crawling work on all the site and can justify a paid option for example. ;)
Regarding Abyss Web Server versions EOL, we usually continue to support all versions (email support) but of course we do not offer patches for older versions. It is safe to say that a version that is 1 year old is probably no more supported since its SSL libraries are probably very old and have security issues.