He was saying he feels like a gambler as he doesn't know if he'll be needing prescriptions or not but since he's in good health he believes the only prescription he'll probably be needing could be an antibiotic once or twice a year. Of course nothing is predictable as health problems can suddenly appear without prior warning.
Are you a type that likes risk or security? This is an interesting question.
I think psychology plays into what we choose for ourselves.