Yes that is okay and you can indicate multiple entries.

Not guaranteed but more likely than not interview will be scheduled.

Depends on the service center processing the case.

Once married you may be adjustment eligible. Consult with an attorney for guidance.

Best to refer to the I765 form instructions for guidance.

No this alone should not detrimentally impact naturalization.

You would indicate that the child will be joining at a later date.

You can contact USCIS before the withdrawal is done.

Yes most likely interview will be scheduled.

Worst case is a denial but try not to think about this until a decision is reached.