I know our lawyer has told us going by car is usually a lot easier, just because they get a lot less traffic flow at the less populated areas and are a bit more easy going. While I was still on my visitor visa, we drove down to the US to get married, then came back up through Prescott (coming to Ontario from New York) and there was very little traffic and the guards were very laid back and easy going. As a comparison, when I came up to Canada the first time, the border security agents in the Toronto airport looked overworked, overhassled, and very mean. I had some trouble dealing with the agent I was given and it has given me nightmares about going to airports now. If it's feasible for you to do, crossing by land is much easier. The only reason we were attempting to fly, my family is in Georgia, and my husband was afraid that our winter tires would be ruined in the very mild winters of the southeastern US.
I'm wondering though, if I at least get my work permit before then, would that be enough to satisfy them and let me back into the country easier?