You should be showing your B1/B2 visa if you plan to enter US as a visitor (for vacation). The port of entry does not matter. Tell the truth - if asked - about having two separate visas.
There is nothing that I can think of that can stop you from filing concurrently if your PD is current. If you are not eligible for I-140 premium processing, file concurrently with a copy of your previous I-140 approval to recapture your PD. I would talk to the attorney to see if there is any...
I would suggest filing for I-140 first without filing concurrently. File for I-140 requesting the PD recapture from your previous I-140 petition (submit a copy of your previous I-140 approval). File for premium processing so that you will know - quickly - within 15 days - if they approve your PD...
Who is going to check at the border? Well, the immigration officers do check. They are well familiar with these tricks and the most familiar question the immigrants face is "How long were you away from Canada?".
-- Does not matter.
-- Citizenship has nothing to do with her visa status. She will not be eligible for H4 before she gets married to you - irrespective of her citizenship.
-- Getting TN requires a job offer that is in the list of TN professions. See how easy will it be for her to get TN...
Yes, I (and so many others on this forum) have done it in the past without a lawyer. Do your homework and get the necessary stuff (proper TN letter, copies of your diploma(s) and your cdn passport) to the border. Getting TN is not difficult at all.
-- Start date can be any; now or any reasonable date. You cannot work for the new employer before your TN is approved. The 240 days period is applicable only when you are renewing your TN for the existing employer. Since you are applying for a new TN for a new employer, it is not applicable to...
"Applying for GC" is a very general term - I guess you should get familiar with the whole GC process (the steps) and come back with the specific questions. The detailed post by CuriousGeorge posted on the forum is very helpful.
-- Where did you learn that IT job market is promising in Canada? In fact, job market in general, in Canada, is not promising at all.
-- Yo cannot apply for work permit without pre-arranged employment.
-- Much faster as compared to the US.
-- I think the rules are similar to the US...
That means you want him to live in the US and commute to work every day. That is not allowed. As a Canadian citizen, he is allowed to visit the US, not live in US. He needs to immigrate in order to live in the US. Yes, the marriage would change that if you are a US citizen. You need to sponsor...
-- No.
-- Yes. (Apply for PR --> Cdn PR --> 3 years of Physical presence in Canada --> Apply for citizenship --> get the citizenship.)
-- No.
This site could be helpful to you: cic.gc.ca
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