Odds of Getting In
Restaurants are always closing— new ones are always springing up to take their place. New upscale establishments will need qualified wine stewards (another name for sommeliers), and if you're in the right place at the right time, you might be able to pounce on the opportunity.
Don't literally pounce on it though—restaurant owners tend not to like it when prospective employees attack with great stealth. That said, there's pretty fierce competition. Higher levels of training and certification help. Who's gonna say no to a master sommelier?