Homeowner getting assignment of his own lien?

Hi, I have a question from a past client.

He has an investment property in San Diego with 2 trust deeds and an HOA lien. Property is titled in his name personally. His 2nd is a LOC that he could not keep up with payments and has gone delinquent. The LOC lender has offered to allow him to settle the LOC for 15 cents on the dollar. He asked if it would be ok for his company to purchase or get assigned the LOC lien and they are open to that. He wants to do this to ensure the HOA doesnt go into second position and decide to foreclose.

His question to me, which I could not find a definitive answer on:
1. Would this be seen as a valid transaction, in case HOA starting making waves. If they ever asked for payoff, could he quote the actual loan balance of what he purchased? Or just what he paid for it?
2. Could his company foreclosure on himself personally to wipe out the HOA lien?
3. If he did get lien assigned, could he modify the loan to increase the interest rate (in exchange for not foreclosing or something) to allow his lien to grow in size.
4. Could his company make all the monthly payments to the first, protecting his position? Allowing his second to grow in size
5. Would it make a difference if his company was single member?

I have run it by 2 lawyers...both of whom said the could not give a definitive answer on what judge would rule on this. Hoping someone on here has some real world knowledge of it. Thanks in advance for assistance.