Purchased in cash far below listing price.

Hiring a property management company will eat away roughly 10% of your rental receipts; however you won't have to worry about creating a contractor list and you may not have to deal with calls at 11:00 at night.Upstate NY is also an option.There are a couple of real estate networking events that meet in NYC.

Walk the talk. 

I am assuming the items below but am unsure if this list is complete and if my estimates are correct for NC. 

Be sure you and your friend are receiving annual forms 1098 associated with both loans and that you discuss with your respective tax advisors.You will purchase hazard insurance in your name, listing the underlying lienholder as 1st loss payee and your friend as 2nd loss payee.When structuring a wrap, it's best for the wrap term to be longer than the term for the underlying loan and of course the monthly P&I payment to be higher. 

All these questions need to be thought of and talked about with your family to ensure everyone is on board and you all support one another.

In previous years there would always be 2-3 multi family properties available in my areas and I’ve only seen 1 new listing for 5 months now.

To be transparent, I haven't started analyzing deals yet but in talking with people familiar with the area I have been told it's hard to find deals that cash flow.

My curiosity includes how timeframes are affected, the listing price of the home, quality of work etc. 

The new listings I have seen are laughably expensive (mortgage is 2x rents for example).