Seems like this is mostly for tear out which is the easy part.

and how do i cover this up?

Can I manage this myself to save on expenses?

I plan to hold this property towards retirement as it's in the area I grew up (obviously anything can change).I am receiving conflicting statements from contractors/friends/family on which roofing option to go with.

Following this.

Asking the MF Group     What's your purpose here, is it to grow your:- Network- Knowledge - IncomeI understand ultimately that these seemingly unrelated dots ARE connected, but why are you here, this is a great opportunity to share your story.

What made you interested in investing in this type of deal?

(Roth's being an exception.)CPA Tom Wheelwright has a chapter on this in his book Tax Free Wealth and agrees with what I just noted. 

You are playing with fire with this strategy to start, but then when you count in an inexperienced rehab to rent a year later, I would earmark this for disaster.

Let's break this down, shall we?