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(since you are Canadian), You do not need any work authorization (TN) to work for a Canadian employer in Canada. It could complicate your tax situation though since Canadian payroll will deduct your taxes in Canada while you are residing/working and paying your taxes in the US.

You will not be eligible for TN since you have a 3 year Diploma (not a 4 year degree) from a non-NAFTA country.

The date of the TN letter and the date of your application. You do not need to show the offer letter (which is different than the letter that is used with the TN application).

The expectation would be to have both dates fairly close - do you get the point?

CBP will not care about how many offers you accepted at a given time. There could be another issue though: CBP will most likely notice the (old) date in your offer letter when you apply for your new TN for Company B. Since the letter would be stale, it could raise the questions regarding the...

Flying out to US is another option. TN can be requested at Pearson PFI while on your way out to the US.

You can work for your US employer from Canada - you do not need any authorization (i.e. TN) for that. If your employer does not have the Canadian counterpart for your payroll, you might want to request them to pay you on the basis of 1099, rather than W2.

TN is not location specific, but is employer specific - you can be anywhere in the USA while working for the employer whose name appears on your TN.

You do not need any compliance letter at the border. You need it only when (and if) you want to register your Canadian Car in the USA - you need it at the DMV office.

TN Category, job responsibilities/description and your degree should match. If not, TN will most likely be denied.

I received my first TN (years ago) at Carway border (where Highway 2 from Calgary meets the border). Go during daytime - this border is not 24x7 - but I think Sweetgrass is (which is slightly farther if you are coming from from Edmonton/Calgary). I received mine in about 15 minutes, no issues.

There is something called "90-day rule" these days - the attorneys wait for 90 days if you are on a single intent status (like TN) before expressing immigrant intent (e.g. filing for I-485). Your company files for I-140 for you (not your husband) and I-140 is NOT an immigrant intent.

Once his I-140 is approved (and when ready for I-485), make sure that you have at least one year+ left on your current TN - so that he can keep working once I-485 is filed. He cannot travel outside of the US when I-485 is filed AND while on TN. With I-485, also file for EAD + Advance Parole...

Your husband can apply for TN (after getting a job offer) while the I-140 is in process. The issue of immigrant intent comes only after filing I-485. The I-485 application makes you ineligible for TN (or any other "immigrant intent" status) - though you can work with the existing TN.

I-130 will be an issue for getting TN - it indicates immigrant intent.

-- The officer at the POE can see your husband's previous/current status in their system - no need to be concerned about that!

-- Documents for the "border TN" should always be Original - because they need to see the originals (they do not keep them). It is always a good idea to keep copies if they ask (in my case, the officer made copies of the Originals before returning them to me). The "mail-in" should always use the...

- Were you previously on TN and then you accepted a new job offer (that required TN)? - Did you already have a (consular) TN visa that was valid at that point? If answer to both these questions is "yes", then most likely your lawyer asked you not to appear for the new (consular) visa - since...

-- *Most likely* you will visit the US customs office. Usually there is a parking lot - you park the car on the US side and go inside the office for any questions. Why do you want to drive 5 hours to San Diego? You could call Nogales to confirm about TN application and go there - it is about an...

-- POE will be quicker - especially if you are in Phoenix. Any approach is ok as long as your paperwork / documents are in order. -- Mail option is better if you are worried about facing the officer (Though I doubt this question will be asked - My TNs were approved - both at the border and by...