But, for non-QM or DSCR products every different products make up there own rules and there 100's of them in the market place.

Skills I am looking to acquire between now and then are how to evaluate residential RE markets, how to accurately forecast property cash flows, and how to make up leasing contracts and evaluate prospective tenants. 

Once you make up your mind to draw outside the margins, the opportunities are limitless.

Yield plus the discounted principal will make up your total return.

There might be a adverse possession/quiet title angle if the 7/8s owner has possession and pays the taxes for the required number of years.My experience is that making offers to owners of partial interests, which I've done several times, makes the players make-up and agree to sell.  

Note that a few of the more onerous requirements are superseded by new state legislation. 

Home insurance is not designed or priced to replace roofs every 5-10 years and then to double down and say that doing so doesn't affect pricing is just nonsense.The roofing practices you mentioned end up getting legislated out of existence (see Florida) because they're untenable.I agree the original poster should explore every avenue but there's no way a legit roofing company is going to be able to "turn this around on the insurance company" in this scenario.

Throughout the course of the project as I was gc'ing it I noticed that the make up of the area was changing.

Yes, you can make up whatever you like.

My Realtor assured me based on comps it would appraise for well over $100,000, so I signed a contingency stating I would make up the difference if it under appraised.