I admit it, I got lost trying to format the reddit post (some comments nsfw) correctly with all the community additions. So I made a better formatted list here because I know how. (Not that I don't want to learn, but today was a busy day, still is sadly).
Then got pointed to this from that site: Old o365 troubleshooter
Which was 'ok' but it pointed me to a newer click-to-run located here: new troubleshooter for O365
This one seems pretty awesome so far:
Clicking Outlook directs to:
Which is a pretty good suite of tests IMO.
My original ask (solved by community maybe, still playing) is the tool Skype for Business Network Assessment Tool.
For reference, the Non-o365 CAT tool as well.
Anyway hope it helps someone troubleshoot.
Edit: not really what I was hoping for, but a MVP put this together in January 2015, nice of him: PDF of Lync/Skype for Biz troubleshooting guide Seems pretty thorough but more oriented towards back-end systems.
Warm thanks to the Redditors for contributing to this list.