Extended stay option after H1b visa expiry date


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My BIL's H1B visa expires by end of November. The employer is not ready to file for extension since they could not source a project for him.
Right now, he is in a medical condition and still hospitalized.
He may not be able to travel back to India by visa ending date and has to extend his stay since he has to complete some more therapies and follow up appointments.

  1. What is the best option left for him, if we have to extend his stay at this point?
  2. Is I-539 a good option to extend his stay?
  3. Can I file B2 for my BIL while he is still in the country?
  4. What supporting documents should I include?
  5. How long can we use existing medical insurance from his employer before we opt for COBRA?
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HE can apply for B2. But not sure who he will pay for medical expense. He can use medical insurance from his employer until he on the pay roll. After that he can opt for COBRA. As per i know for COBRA if employer is not paying he will have to pay by him self 100% and it will be at least around 1K. 

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