Will there be excess supply of houses in the years to come after the baby boomers are no longer living in single family housing?

Additionally, when completing the refi the reason supplied for doing the cash Out Refi would raise some eyebrows I would presume, but I figured the bank would just ensure those people are actually paid off much like they would with a reason being for a cash out to pay off or consolidate debt with me keeping the excess cash.

I am in Pittsburgh so I dont know if the process is different in your area but sometimes you cant sell the property with good title for up to 1 year so your holding costs can be excessive.

I agree that charging each landlord $250 to maintain this list is excessive.

To address that, we underwrite our deals to a 10 year hold, with 10 year financing and excess cash reserves.

An umbrella policy provides excess liability coverage above and beyond your underlying policies for those worst case scenarios.

She entrusted me to attempt to negotiate the selling of the house with a favorable outcome.I went through two attempts to arrange a Short Sale with local investor that I found via loose social channels. 

Bank isn't gonna let you loose their money.

I have seen swat teams raid neighboring units managed by slum lords who didn't screen tenants, I have dealt with abusive boyfriends putting my tenant in the hospital, broken down cars (which leads to them missing work because they can't afford to fix the car, which then leads to them loosing their job and then getting behind on rent), being threatened with a gun (guy lifted up his shirt showing me the gun in his belt), to countless sob stories. 

While the cash flow seems ok, i'm worried when it comes time to sell, it wouldn't make sense because if banks won't lend on it, then you loose a HUGE buyer pool.