Crossing the board by road (USA to Canada) on Work Permit

Hi,
We will be relocating from USA to Canada for first time by driving the Car through Detroit – Michigan to Toronto after receiving the passport back from VAC this week.
Few Questions,

  1. Will there be any challenge in getting work permit stamped on passport at Port of Entry when crossing the border by land?
  2. Does any ones traveled by Car during first time landing from US to Canada, please any list of documents required and experience
  3. Wil there be any restriction like only few ports of entry (around New York) only will issue work permit stamping on passport or all ports will do it (like Detroit)?
    Thanks!