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Flagpoling for new TN

I'm supposed to start a job in Nevada in September. I'm flying out to Nevada a week and half before the job start. Last year I was denied a TN at YYZ for another job because the lawyer forgot to include dates of the job in the letter.
I'm thinking of driving to Peace Bridge two weeks before my start date to apply for the TN there instead of the day I fly out. I need to purchase health insurance for the 3 months before the job's benefits kick in but don't want to spend all that money and end up getting denied the visa. I've been unemployed for months and just trying to financially manage through this pandemic jobless hell.
I'm an essential worker in health and exempt from quarantining in Canada.
Has anyone tried flagpoling at land borders recently? Is this generally a bad plan and I should just wait till the day I fly out at YYZ?

submitted by /u/TwistVivid
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source https://www.reddit.com/r/immigration/comments/i46ca1/flagpoling_for_new_tn/
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