You probably have to start at smaller local skating rinks.
I actually used to have a book about weird jobs, and how to get into them. Wish I knew where it was.
Zamboni driver was one of the jobs that I had highlighted as something I thought would be cool. I think the average salary was also pretty decent, at like 40+ per year, and this was back in the mid 90's. I'd imagine the guys doing the NHL arenas were the ones driving up that average.
The other job that I thought sounded great was blimp pilot, but that's a tough one to get into, as there's really just not a whole lotta blimps out there.