Will I able to get in the US with a tourist visa B-2 after being there for 2 years with a J-1?

I am afraid you will be extensively questioned and could even be denied admission if returning so soon, for "tourism" purposes, unless can show to...

If i get payment for my visa extension will the "two year do not apply" status change for me?

I agree - the only way to ascertain whether the 2 year rule applies to your program or not is to check that on DOS' "Skills List."

Simply apply for a US passport and see what happens. I strongly recommend to also apply for N-600, even if obtain a US passport.

Can I answer No to questions 17 and 18 of Part 8 Form I-485 if I fell out of F1 student status?

"Yes" to the first question and "no" to the second one.

What should i put on from 765 question 27?

Yes, in your case (c)(9) is the correct one.

Yes, you will need to present a new/updated medical exam at the interview, given that yours will have expired.

Trying to find away to get my mother-in-law here to visit with her grandchildren for Christmas ?

Will likely not happen. Need to be patient until your spouse naturalizes and can petition for his/her mother to immigrate to the USA.

Impact of Previous employer's fraud on H1 extension, 3 years after transfer to current employer.

I couldn't agree more. You will need to lawyer up as soon as contacted by any of those agencies. Do not agree to talk to them on your own.

Can I stay beyond my h1-b expiration if I have a self NIW petition of I-140 pending for 10 months, I have just filed an I-485 ?

Yes, as long as you were in valid non-immigrant status at the time when filed the I-485.

Can engagement or marriage lead to denial of entry on a student visa?

These kinds of strategy questions are not meant for a general blog such as Avvo.