We all have seen the advice to get a ski-related job if you want to a) ski more, b) ski cheaper, and c) get better fast. That certainly worked for my husband and me. It also provided our children access to the sport. I would go so far as to credit the love of skiing that they learned in childhood for being part of what motivates them to find jobs that pay enough money to afford skiing (and golf). So of course I would say that my ski-job has been very, very good to me (though my social security benefits wouldn't qualify me to live under a bridge).
But there can be a some downside to working at what you love. Does working at it take some of the joy out of skiing? What happens to the pleasure when it becomes vicariously enjoyed through "clients"?