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.

That is called OSB ( oriented strand board) and is mostly used for sheathing on the outside of the house under the siding. the problem with putting Spackle over it to try and hide it is that the moisture from the Spackle may get into the board and start to de-laminate it. if it is only 3'-4' high, you can dress it up with some sheets of 1/4" bead board, if it's the total wall you can cover it with 1/4" drywall. look at it this way, there is no way a tenant will put a hole through those walls after you cover it, i would consider having that a plus.

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.

Use a moisture meter outside and inside. 

If it was a flat surface we would simply install quarter round with clear caulking to act as the moisture barrier and keeping the flooring down.

I set aside a large portion of my excess income that I use for investing.