(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.
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).
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...
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.
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.
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.
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