This will be my first purchase so I am trying to tie up all the foreseeable problems before i offer so i can make sure the offer is to my advantage.  

If he seller finances, his net worth remains the same, trades property for a note.

The wealth advisor seemed to have a good point that banks like to see the value of the life insurance policy/type of policy as assignable so if you pass while covered, it can meet your obligations, then the remaining is left for family/spouse children.Any truth in this, and could this potentially sway commercial lending apps one way or the other?

I like not using lawyers a lot, but in this case you have personal ties to these people. 

Many people have made mistakes even in "passive" TK so if you don't have a cushion or can't sleep at night because all your money is tied up in one TK and you can't sleep every time something goes wrong  it may be problematic.While most people say being in NYC is tough to get started and they are right there is one thing that is good about NYC which is that the values are high.

So most brokers/agents will be looking for a qualified buyer with some down to direct purchase or an all cash buyer.Any broker/agent worth anything will not let a wholesaler with little or no cash to close tie up a property with little to nothing down.

If under water, then likely the HOA or an investor will be the only bidders, and both will want it to remain rented.

When these tenants asked to remain in their existing unit, and still pay the increased rent, we sent our cleaning service in (at our expense) to thoroughly clean the apartment from top to bottom.  

In small towns there is a lot less competition from a buyer standpoint so take advantage of that in negotiating your buy price.In order to make small town real estate work (at least on a larger scale), I think it is imperative that you be tied into the local community. 

The WHERE is powerful, and you can hear Joe’s tips on determining your “where” in this episode.As Simon Senek says, you’ve got to “start with WHY.”The “WHY” behind your business is what Joe Evangelisti says ties all the other W’s together.