I would recommend not to squeeze investor too much as if things go well he will have the appetite to come back with you and refer to outside people.Absolutely consult a lawyer when taking investor money.

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

I called every lender in my local area and took notes, asking about their appetite for SFR lending.

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.

The appetite for real estate has been insatiable in Boston lately but I also sold a three-family property to another client on Nightingale Street, Dorchester for only $112,500 during the bottom of the Great Recession so it's important to keep perspective which this market, in my opinion, seems to have lost.

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

If I lived in an area hostile to landlords or a place with a voracious appetite for tax dollars I'd certainly consider investing outside my home area (actually I'd probably consider moving), but I think it would be hard owning property that I can't work on, see, or visually inspect easily. 

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