TN Visa for remote jobs

My TN is up for renewal (Jan 2021), our employer drafted a letter to the POE and we kept everything ready, they will issue me the letter sometime end of Dec, 2020

They wrote in the letter saying that I am already working with them and they will require my services for another 36 months like that... they added this paragraph on the first page of the letter itself

Not sure, if this is a requirement as every time we go to Border for TN, its considered as new TN

Do you have a choice between USCIS 1-129 app and going to POE ?.
 
The letter is not to establish whether you are qualified for the job -- the firm wouldn't be hiring you otherwise. The letter is to establish that the JOB qualifies for TN. The applicant (not the letter) then furnishes proof that they qualify for TN (citizenship, education, etc),
 
do I need to obtain a TN visa if I am working as a Canadian contractor on C2C basis for a US company? Assuming that I will be physically residing in canada and infrequently needs to visit the US client which will be most likely once every 4 to 5 months.
 
Even if The US employer hires me as a Canadian contractor and if I am living in canada?
CRA is fairly strict on the contractor relationship. More so than the IRS, in my experience. If you're in a full-time and ongoing relationship, consider using a PEO instead. Then there's a business-to-business relationship across the border but CRA is happy.
 
Yes, the PEO is really the only way to be a Cdn resident/employee of a US company and not run afoul of CRA, and not encumber y=the US firm with Cdn tax/reporting.
 
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