--Take out the HELOC on the rental and my stockpiled cash and pay off the mortgage on my main home in full and call it a day until the crash comes along when I will have likely saved up more money and have equity in my home, but of an unknown amount.

Just curious if anyone has every had experience with raw land that shows up on the tax records as the owner being "unknown"?

I would not do this considering your current debts and the unknowns about where you will end up after residency.

I really would like to get this closed but have the unknown of having a destroyed unit without a tenant security deposit in place.

We've been hunting for a couple of years and it was hard to get over the fear of the unknown for me, but this deal was too hard to pass up.

Ideally, we'd like to achieve owner financing for the purchases but also have the possibility to get commercial financing.I find myself with a small but highly targeted list - owners of more than 10 residential properties - their motivation to sell is a huge unknown for me.  

Don’t fault him too hard because by and Large His response is very typical of most people who share his ideology of getting paid as an employee .his thoughts on investing in real estate are solely based in fear because he is not educated on the subject and Fear comes from the unknown .

You might put a contingency clause that will allow you to walk away if you find anything unknown on the title of the subject property. 

You cant put a $$ per sq ft number on an unknown 

Having plans established quantities and eliminates the unknowns.