OPT cancellation and I-485

You really need to discuss the plan with your DSO to see if he can issue a new I-20. Perhaps you should met with an attorney in-person to review...

Do I need a waiver?

You may need a waiver because of your deportation. Regardless, you will need someone who can file a visa petition and get the process started.

Filing I-730 & I-130 concurrently

You will certainly encounter questions as to why you did not include him on your asylum application before and also marked that you were single.

You appear eligible from the information you have provided but you really should have an in-person consultation to make sure.

When will I be eligible to apply for US Citizenship?

Your five years as a resident will occur in one year on 01/17/2017. You can apply for citizenship three months before that - so on 10/17/2016 you...

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H1B transfer and 8th year extension

Yes you can extend your visa in one year increments.

Do I need two separate I-130 forms? Where is the Arrival/Departure Record (I-94) from? Submit I-485 form at the same time?

You must submit separate forms for each. If you are currently an American citizen then you can file concurrent I-130 and I-485 applications for...

Yes you can be denied because of a 9 year old DUI but it is not likely.

Can I apply for asylum while I am also applying for a reinstatement of my F-1 visa?

Yes you can apply for asylum even if you are applying for reinstatement of your student status.

I am on H4EAD, can I rent my house as we are moving to different place.

Yes you can rent your house if you have to move to another area.