Odds of Getting In
It's pretty easy to begin a career as a repo man. You don't need a degree or special schooling to become a repo man. You can get your foot in the door by seeking out a reputable company or repo agent, who can show you the proverbial ropes. Many successful repo agents get started by working with another agent or repossession company. It's also not a flooded career market, which means it should be relatively easy to find someone to hire you.
But repo companies don't want to hire people who will fail. Makes 'em look bad to the banks. However, once you've established yourself and get the hang of the business, you can always branch out on your own.