It all depend on what will make you sleep better at night.If you are expending your business and expecting to grow your asset over the next few years, it may be worth starting having the structure in place for it.Using LLC to hold your properties should be tax neutral.

Lets say I can work out a deal with him and he can maintain his current bank mortgage,  What legal papers between me and him would let me be able to deduct the mortgage interest and taxes, when those mortgage docs would still go to my buddy with his name on em?

Even when you just over see the property you need to keep stocked on tp, paper towels, salt, pepper, spices, cleaning up the grill, etc.

Have an attorney draw up paper work.

You might be able to find some clever ways on paper to make it happen.

I couldn't locate the property to run rent comps based on the address, but if you're getting negative cash flow on paper, you may want to investigate things closer.

No matter what they are on paper or even in person, you are dealing with people and people are unpredictable.  

Right now, on paper, they have annual appreciation returns of between 5.45% to 12.92%.While it hasn't appreciated too well, IT'S A GREAT NEIGHBORHOOD FOR A RENTAL.

Although I have some income from direct marketing and book sales, for many years 95% or more has come from real estate but different aspects of it like rentals, flips, holding paper and managing/contracting.

If not, on paper you're basically paying people to apply for your rental by covering a portion of the application cost.