I realize that it all sounds very restrictive (and it is), you have to remember that once you're on Canadian soil, you can get most of the rights and privileges that a Canadian gets including health care while your "legal/illegal" status is figured out through the courts.
We've got a ton of "non-status" people in the country who we can't deport because their cases/appeals haven't finished, but to whom we have to provide the basic of Canadian rights (food, housing, healthcare, legal aid, etc.)
Visitor permits are easy to get, permits to live and work here....not so much.
A. The OP asked about "working" in Canada.
B. There is no such thing as "visitor permit", it's called a passport. Anyone from the states can "vacation" in Canada unless of course you have a felony record. It which case they will not let you in the country. Keep in mind, a DUI is a felony in Canada and that counts too. If you have only 1 conviction and it was more than 10 years ago, and you can "prove" that with a copy of your criminal record you can still get in. However, it is up to the border agent's discretion.
C. In BC anyway, there is a 30 day waiting period for the provincial healthcare plan and it is not free unless you are indigent (or have sufficiently low income).
D. US Citizens are not granted "landed immigrant" status like those from other countries.
Sorry, but you sir are just plain mistaken (on several fronts).
If you don't need to work, don't have a criminal record, and have a current passport you can visit the Great White North whenever you choose. However, why Whistler is beyond me. I have friends who were volunteer ski safety "yellow jackets" at Whistler for years and the concrete they call powder there sucks, it's overpriced, and mobbed by like 20,000 tourists at most times (many of whom can't ski or board for shit). Per my friends who were locals and there 3 days/week for several years.
There are cheaper and better mountains to be found in BC. From what I hear, Revelstoke is the shit and Kicking Horse is good too.
Anyway, hope that helps.
PS: Stay away from Shames, I here it sucks there.