@mitu well that was a good hint. Even though tracert and ping tests checked out, a faulty network cable was still the culprit. Must have just been enough to connect somehow.
@buzz I am using the right port (the normal output one), and it works fine, then all of the sudden it blanks out, unplugging and replugging seems to help.
@Thorr69 It depends on how they did it. If you use the Retropie script, you can update the Retropie portion up to 4.4 on Jessie Raspbian. Version 4.5 dropped Jessie support and you had to start fresh to upgrade to 4.5. If you attempt to upgrade the distro underneath, that is where the problems quickly come into play.