Another observation
If i select Play from the popup menu i see a little window open and close almost instantly (almost like a cmd window?). If I choose Open With -> RetroArch -> mame_libretro, the RetroArch UI widget launches before crashing.
By comparison, when i run straight through RA this same RA UI appears, disappears, and reappears as its loading the game, which eventually works.
Derp:
The crossed out section was a result of me putting command line params in the specific ROM itself. Removing those makes the behavior match the un-crossed out text.