EmulationStation has the X button mapped for choosing a random system or game. If you're in the system list, X will position you to a random system, if you're in a game list (inside a system), it will position you to a random game - you just have to press A to start the game.
Modifying the existing behavior - to start the game automatically - means you're going to have to program it into EmulationStation - something that's non-trivial for someone that's not familiar with programming or EmulationStation's source.
verbose mode appears no where the link several people have refered be to.
The option is in the Runcommand menu, but the screenshot/example of that menu is likely old and does not show that choice as an example. However, if you use Runcommand, L "Launch with verbose logging" is an option.