You will probably need help(hire your own sharks, ie brokers, lawyers) and have to pay for it accordingly.Lastly, the above pain points are all manageable if you are prepared(good brokers/partners and realistic planning) and well funded.

Of course, you should ask a real estate specific lawyer familiar with your state's laws but from what you laid out here, I see nothing illegal.

I don't know, you're in the gray area (believe me I'm not against paying an honest referral fee).I think the word salad is you need a real estate license if you're arranging the sale of RE in expectation of a fee.DISCLOSURE - AM NOT A LAWYER SO I MAKE MISTAKES AND MAY NOT BE CORRECT!

Odds are, unless the prop is a real mess, it will not sell for less than debt + lawyer fees + penalties. 

After 27% to lawyers and other legal costs, the proposed payout is about 11% of the amount owed with the remaining $300K+.

You need to build these relationships, and I would include other real estate professionals such as lenders, accountants, lawyers, etc., who could potentially share with you an opportunity they know of.

Something I did not mention in the original post was setting up a lease, my guess is that the best bet is to find a boiler plate for the state you reside and then consult with a lawyer to custom fit it to your needs?

The best discussion we've had was to have a lawyer help out for the the LLC to assume the mortgage with the personal.  

@Charles Chiu I am not a lawyer.

It would be better to contact a lawyer specializing in this issue to give you an answer relevant to you.