By the way BCguy, for Question Number 1.
1. I am a Filipino and do not have a U.S. visa. My question is, can I apply for a work permit at the border even though I do not have a U.S. visa? I have all requirements ready - LMO, job offer, medical, etc.YES
I am a Visitor's Visa holder for Canada. My visa is valid until December 2010. Is the answer to this a YES still?
I believe the answer would still be yes. Did you apply for a work permit elsewhere? Manila? 'Cause you don't really get your medical results if you never applied for it in a consulate. If yes, then most likely you would also have been given a letter (if your TWP was "approved") from the consulate recommending you to the immigration officer to issue the work permit for you. You don't need to pass the US for this, and you don't really need to be at the US-Canada border, you just need a port of entry - like an airport.
Is your visitor's visa of type "Visitor" or "Worker"? Did the consulate give you this alongwith your work permit application or was it a different/tourist application? I had my TRV (temporary residence visa, it's the visitor visa) stamped on my passport by the consulate. Your entry to canada actually depends on this (the work permit is not a visa, but a permit. it doesn't allow you to enter Canada if you have no, or an expired TRV).