My concern is that the attorney who is advising him is the same one who works with the shady investor...

You probably need to ask an attorney.

Because the IRS attorneys only want to go forward with cases that are a slam dunk, black & white win for them.

I have friends from their but I would definitely get the India equivalent of an attorney for advice. 

I'd rather rip off the bandaid, and pay the $1k to an attorney for removal, so it stops messing with my psyche.

Hi @Charlie MacPherson, I don't have a specific private money strategy for you, though I would counsel that once you have a decent proposal/informal deal idea worked out, the next most critical piece will be getting a sit down conversation with yourself, your client, and your client's bankruptcy attorney.

As always, please confirm anything I (or anyone else on BP) says with your attorney (and perhaps a CPA).I'd definitely double-check with the HML to see if they're okay with you receiving secondary financing. 

However, maybe explore buying a trust, but talk to an attorney about that one. 

I understand that in order to begin this journey, I'm going to need a team (i.e. accountant, contractor, attorney, etc.)

That way you maintain Attorney Client Privilege without getting to much info about yourself publicly