• As for the "new machine" and "new cable".
    I was using a Chromebook Pixel that now has Ubuntu 19.04 Installed and it seemed to be the problem.
    I have another Chromebook (the original CR48) with Ubuntu 18.04 and it doesn't seem to have any trouble.
    The fix ended up being again with simply a newcable. Nothing special. And using a windows desktop computer without a hub. I can't figure out if there is a small change in the ESPTOOL.PY line that made the difference. but I was able to then run the script and build two esp8266 and that worked on the CR48 ubuntu machine, a Macbook Pro 2016 and a windows 10 machine all working now.

    The Top of the linue Ubuntu box doesn't work and I frankly can't figure out why. It's able to use other arduino devices just fine and is my main computer for everythign else.

    and of coruse my amazing Pixl.js device works on that perfectly but of course that's through bluetooth.