The message about the controller being detected / configured means that RetroArch starts ok. Can you try and enable verbose logging from the Runcommand launch menu when running the game, then exit the game and copy the /dev/shm/runcommand.log file over. Post it's contents on pastebin.com to take a look at what might be the error.
You'll probably need to enable SSH and use WinSCP to copy that file, since it's not available via file shares.

@joe-info

Solved.
Dtparam audio on fixed the drastic boot issue

@echotech26 probably wrong romset. You need to read through the arcade documentation.

@NoobishPi Try renaming the configuration file - https://retropie.org.uk/docs/Playstation-1/#pcsx-rearmed-controls.

Okay, I'm not sure what happened, but suddenly Genesis games work. I'm not sure if it was bad roms like @mitu said or if it was bad naming conventions on my end (changed both at the same time), but seems to function now either way.

Thanks again everyone for the help!