What will most likely happen in my second immigration marriage interview? What will happen if I fail it?

I agree with my colleagues. Please seek advice from qualified counsel.

Would my H1b visa approval be jeopardized?

I agree with my colleague, not clear what you are doing if you already have the visa.

Are Canadians allowed to work and live in the US, or do they need to apply for a green card?

Canadians can live and work in the US provided they have the proper visa. In addition to employment based visas available to all foreign nationals,...

Can i be denied deferred action for working under the table...?

Unlikely. For the exact reason stated by my colleague.

Form I-821D. Do you need a lawyer to file the form or can one person do it himself?

You would not get disqualified for being married to a US Citizen. Did you pay the tickets and handle the warrants?

Can we file for divorce in the US if we are under a non-immigrant B1 visa status?

I agree with my colleague, the fact that marriage took place in another country is irrelevant for the most part. You should contact a family law...

I-751 waiver: decided to get divorced only 11 months after conditional green card. red flag?

Red flag, sure, but as my colleague states, not a determining factor. Remember the issue is good-faith marriage.

Deferred Action for me? Came in 1993 (11) years and left. Came in 96-97 (14) junior high. came 99-01 high school. (17-18).

I actually disagree with my colleague. It looks like you qualify. The question is whether or not to file with that background, but you do...

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I made a mistake on my I-821D submitted package.. I put country of residence: Mexico instead of USA

Actually, DHS define s Country of Residence as "the country in which an alien habitually resided prior to entering the United States." ...

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What documents do I have to prepare for R2 status and if I got R2 status, can I get social security number?

My colleague is correct.