My situation is very similar to the OP but I didn't see a clear answer on their question.
My
TN for my full-time employer is expiring on the 28th of June. I also hold two TN's for contract employment both of which are good for another 11 months. I need to renew/get a new visa for the full-time employer but due to the timing of it want to be able to incorporate a vacation over Canada Day and would most likely be applying for the visa on July 3. I will also be receiving a paycheck during this time as well. Is it more difficult to renew the visa after it's expired even if I have two current TN's allowing me to work in the US?
I don't want to jeopardize my situation but also don't want to shell out a lot of money for four flights. Any advice?