Border Crossing to Canada - Employment

Hi..

I am new to these boards and am actively searching for information regarding our upcoming move to Canada.

I am Canadian. I will be getting my updated passport within a few weeks (had to wait for my citizenship certificate to be mailed, which it was - last week).

My husband (US citizen) is accepting a transfer with his company to Ontario. He will be leaving in mid-December to go up, find a place for us to rent and complete the necessary process for working in Canada, returning to the US within a week to help me with driving the car to Canada.

Here is my question: can someone tell me about the crossing process? I read that there are 2 interviews and if all paperwork is in order, these go relatively quickly. Is this so?

Could he experience issues if he returns to help me with driving my car to Canada? (IE: they allow him to cross the first time but could he encounter a border agent who decides NOT to let him cross again) ? or is the work visa for him issued the first time he crosses? I wasn't sure how long it takes for that to be issued.

Thank you for your assistance ! I appreciate it.