You'll have to make assumptions and have some fear when you move on a property.

And, importantly, fear around my ability to confidently show the Seller that the deal I am proposing is one that CAN help solve their challenge or problem (once I find out what that is!). 

At the same time, I fear that a new tenant might stay there for ever and interfere with the sale at a future date.

Although, there is really nothing to be feared as long as you know the laws and treat people fairly.As mentioned above, finding a quality renter is really where all the heavy lifting is done. 

I think he should have given it straight and explained the service as a comfort for those not saavy enough to negotiate through the situation, not wealthy enough pay it off, or fearful of bad credit scores with a refinance.

Most people enter partnerships because of FEAR, or want of COMPANIONSHIP not any real benefit.  

I am convinced at this point to go ahead and list on both, I think it's going to be less of a cost than I had feared.

The starting point is knowing what emotional drivers (desires, fears, hopes) lead people to spend money on a unit such as yours.

I've been wary about jumping on deals now for fear of a cycle change and much more deals being available a year from now or whenever.

Fear and worries don't really exist.