IANAL, but technically speaking, the TN visa isn't dual intent, which means you're not supposed to have it, live in America, and then switch to a green card (permanent residency). More specially, applying for the green card, I think, violates the terms of the TN visa. All that said, I think this is a common thing Canadians do (as a Canadian living in America, having seen it first hand).

Essentially you would come on the TN visa, and then begin the green card process based. About half way through this process (maybe 1 to 2 years after starting), you enter a six month ish phase where you can't leave the country, because if you did, there's no guarantee the border agent would let you back into the country. Once that phase is done, you should get your green card and be good to go.

The other thing to note is that your dependents can't work on the TD visa they would get, unless they have their own work authorization (e.g. their own TN visa, are dual citizens, etc.).

There are other options, like the L1 visa, which has different requirements (you have to be a manager and have been working for the company for a year IIRC), or of course the H1B if you win the lottery.

Altogether the TN is, imo, a pretty good way to go.

Appreciate your response. You pretty much addressed some of my concerns