Welcome to EpicSki, Emily!
Yes, I'm 99.9% sure that a Winter Park employee pass will get you to Steamboat, as well as Copper Mountain in Summit County. Others have mentioned that Winter Park is an Intrawest resort, along with Copper and Steamboat, and employees have long had the advantage of the Real Deal exchange program with many resorts in Colorado--almost all except the Vail Resorts areas (Keystone, Breckenridge, Vail, and Beaver Creek). But a VR pass gets you a lot of great skiing in close proximity. The tradeoff is yours to weigh.
I too disagree that Keystone's skiing is "crappy"--I think it is one of the most commonly under-rated resorts in Colorado. It has a lot of very good skiing, for all levels and interests and, while it is limited in truly extreme backcountry steeps, the terrain available to those who know where to find it, either by hiking or snowcat, will challenge anyone. If you don't believe it, come sign up for a private lesson with one of Keystone's top instructors who can show you around. Unfortunately, Keystone still suffers from the reputation it once deserved, long ago, before the North Peak and Outback developments, as nothing but long, groomed cruisers. There is a lot more!
Of course, there is great skiing at Winter Park/Mary Jane too, and they do tend to get consistently great snow. The choice is yours. You'll be happy skiing either way.
However, if your goal really is "to make excellent money and have more than one job and so on," you should perhaps rethink your plans entirely. Working at a ski resort can be a lot of fun, and truly rewarding in many ways. But you aren't going to get rich. And if you're going to work multiple jobs to try to get rich, what's the point of living in the paradise of a ski resort? Looking out the window at people skiing isn't that much fun!
Good luck. If you have questions about Keystone, I'll be glad to help.