With regard to your third option, I don't think that is a terrible idea if paying cheap rent.

The best part is, once you get there, the train is ready to take off to the next milestone.

However, I'm not sure what the "specialist" part is referencing.  

We have run into several different scenarios, including a lending company who was working with a 3rd party lender that had "organizational" issues, so, after nearly 3 months of dragging their feet, they were not able to help us (wasted our time, plus the cost of an appraisal).

I am not too happy with it but heck, it's a rental.Now, I have another one in another property that cracked...and a third one that chipped.So I am looking for ideas what I should do with these. 

Is the modification initialed by all parties?

So far you've witnessed what have essentially been two full-scale proof-of-excess moisture experiments, and are very possibly headed for a third.  

There are no financial compliance issues with financing from related family.There are financing issues when you finance to an unrelated owner occupied party, Dodd-Frank is not the only issue.

Essentially, you are paying for something you hope you never have to use....but if it does happen, you have multiple parties in your corner fighting off a claim, for many years if needs be, and even if the limits of one were exhausted, you have another...and the legal fees alone could be large, so nice to have the insurers footing that bill and having an interested in settling or disposing of the suit....great question, though, could you be overinsured?

Obligations under a unilateral contract cannot be assigned without consent, bilateral contracts may be assigned unless restricted, a real estate sale contract is a bilateral contract both parties agree to do something.