If you can make friends and get to know people and LIKE people, then you can deploy that relationship in a manner for all to make money.

As an example, were the occupants are already in tenancy, you may be able to ask them to remit a security deposit, but you may not be able to compel them.  

I hope I've explained my idea in a manner where someone with the experience can chime in.

Take a property like that, on the MLS, pay market value even for its current state, and unlock the hidden value by adding beds and baths in a cost effective manner (converting attics and/or basements, converting the garage and then adding a detached garage structure, etc).

Your job at this point is to listen to your DB, stay calm, and communicate in a very businesslike manner.

My take on your scenario is that you returned the bulk in a timely manner; so the amount of the deduction is the most that can be doubled IMO.

Lender paid single premium typically means that the lender is bumping up the interest rate, above market rate, and paying off the lump sum charge from the insurance company in that manner.

A few years ago he was Dollar cost averaging, then  all about buying property in the bay area, then he was doing side hustles with friends to buy properties with negative cash flow, then he had a portfolio with a couple of momentum stocks, then he went to all gold, then has been selling some of his houses and been dabbling in all manner of stocks of development play miners, and believes the stock market is massively over priced.  

Back this up with the 60 day notice served properly.Find out if there are any barriers he faces to getting the stuff out in a timely manner.

At the same time I will start the forclosure process to cover myself, and compel him to sell it.