Get professional help NOW. Your IRA is exempt, doing what you suggest only would mean you could lose it, and the house, when losing neither is actually possible.
As long as you keep paying both mortgages, you can keep both houses.
Yes he can file for Bankruptcy if he wants to depending on the situation of his property.
Chapter 7 is a liquidation bankruptcy, you are giving up your assets. If you want to keep your home and car you would need to file a Chapter 11 Bankruptcy.
yes
Yes.
yes
It depends on which "chapter" of bankruptcy you file. I suggest you speak with an attorney to see what you can do.
Yes, as long as you keep making the payments.
Generally ten years from the time of the last (closing) activity of the said bankruptcy.
if your legally married when you file bankruptcy, you must include every single asset including the spouses. depends on what type of bk you file. you may be able to keep your assets.
yes
sometimes but barley ever